road trips from boston in summer

New England Wanderlust

Connecticut , Maine , Massachusetts , New Hampshire , New York , Rhode Island , Vermont  ·  March 30, 2022

34 Awesome Road Trips From Boston & Best Itineraries (2024)

Boston is an amazing starting point for adventures all over New England and the Northeast. With so many options to visit tons of nearby coastal towns, exciting cities and plenty of quaint, charming villages, there are endless possibilities for road trips from Boston. And since I’ve been road-tripping and traveling all over the Northeast for over 10 years now, I know all the destinations that are worth your time.

This list includes destinations that are all individually under 6 hours from Boston, and if you’re looking for road trip itineraries that combine destinations from this list, be sure to scroll to the end for suggested itineraries to make the most of your road trip!

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Best Road Trips From Boston

For this list, I’ve broken down the destinations into four categories: Coastal, City, Charming Towns and Luxury Getaways. For each destination, I’ve also included the time it takes to get there from Boston, highlights of the best things to do, what to expect once there, and nearby things to do.

Coastal Road Trip Destinations From Boston

1. plymouth, ma.

Distance From Boston: 40-50 minutes

If you’re looking for a quick, easy getaway from city life in Boston, a little road trip to Plymouth is a fun way to do that. While the town is known for its history dating back to the early 1600s, they are also lots of outdoor activities, parks and beaches, and combine that with a small-town feel, Plymouth makes for a lovely little escape from Boston.

Best things to do in Plymouth:

• Plimoth Patuxet Museum is a living replica of the original pilgrim colony settlement. If you’re a history buff, this is a must-see. You can even climb aboard the Mayflower II, an exact replica of the ship that brought the pilgrims to Plymouth.
• Plymouth Long Beach is a 3-mile long stretch of public beach that’s perfect for getting out by the water.
• Plymouth Farmer’s Market is held every Thursday from May through October, and was Yankee Magazine editor’s pick for best Farmer’s Market in 2018.
• Brewster Gardens is a tranquil, waterfront park that’s sure to invite lots of relaxation.
• Walk around the charming downtown to visit the shops and restaurants,
• Pop into Dirty Water Distillery for an artisanal spirits tasting.
• Go on a whale watch tour with Captain John’s Boat Tours .
• Spend the day getting pampered at Mirbeau Resort & Spa , and even stay for lunch or dinner, or the night for the ultimate day of relaxation.

Click here to book your stay at Mirbeau Resort & Spa!

Psst! I have an entire post on visiting Plymouth, MA , if you need more ideas!

2. Cape Cod, MA

Distance From Boston: 1-2.5 hours, depending on where you to choose to go on Cape Cod.

With over 500 miles of shoreline to explore, Cape Cod is the ultimate beach road trip from Boston because you can get there in about 2 hours and feel like you’re in a whole other world. There are 15 towns in Cape Cod to choose from for your visit, and more beaches than anyone can count. Fill your days being ocean-side, exploring beautiful little coastal towns, eating fresh seafood and taking in amazing sunsets.

Best Things To Do on Cape Cod :

• Visit The Cape Cod National Seashore
• Explore Chatham’s downtown
• Visit Provincetown and the Pilgrim Monument
• For more on the best things to do on the Cape, click the link below for my detailed travel guide.

You may also enjoy:

• Can’t Miss Things To Do When Visiting Cape Cod For The First Time
• Best Things To Do On Cape Cod For Adults
• Best Towns To Stay In On Cape Cod
• What To Pack For Cape Cod
• Unique Things To Do On Cape Cod

3. Nantucket, MA

Distance From Boston: 2-3 hours, which includes time to park at the ferry terminal, and ride the ferry.

Nantucket is a gorgeous island off the coast of Cape Cod bursting with charm and natural beauty. A day trip to Nantucket is common while visiting Cape Cod, but staying overnight for a night or two would be the best way to make the most of your road trip from Boston. This is a great island to explore if you’re looking for stunning beaches and a beautiful downtown area.

To get to Nantucket, you’ll need to take the ferry from Hyannis on Cape Cod. From there, you can choose between Hyline Cruises or Steamship Authority to get to Nantucket.

Best Things To Do on Nantucket:

• Explore the shops and restaurants in the main town.
• Visit Brant Point Lighthouse.
• Rent a moped to explore the local beaches and towns.
• For more amazing things to do on Nantucket, click the link below for my detail travel guide on a Nantucket day trip.
• The Best Nantucket Day Trip Travel Guide
• How Many Days Do You Need On Nantucket + Suggested Itineraries
• How To Visit All The Nantucket Lighthouses

4. Martha’s Vineyard, MA

Martha’s Vineyard is the other island off the coast of Cape Cod, and it’s more popular as an overnight destination, versus a day trip because it’s bigger. Comprised of 6 beautiful towns, Martha’s Vineyard is home to beautiful beaches, quaint Main Streets for shopping and dramatic cliff-lined shores.

To get to Martha’s Vineyard, you’ll need to take a ferry from either Woods Hole or Hyannis (both terminals located on Cape Cod). There is no benefit to picking one over the other, and it’s best to just pick whichever location is more convenient for you (usually it’s Hyannis for most people).

Best Things To Do on Martha’s Vineyard:

• Gingerbread Cottages in Oak Bluffs
• Edgartown downtown and lighthouse
• Aquinnah Cliffs and Gay Head Lighthouse
• South/Katama Beach
• For more information on visiting Martha’s Vineyard, click the link below for my guide on deciding between Nantucket or Martha’s Vineyard for a day trip.

You may also find these Martha’s Vineyard posts helpful:

• Is Nantucket or Martha’s Vineyard Better For A Day Trip?
• The Ultimate Martha’s Vineyard Day Trip Guide
• How To See Martha’s Vineyard Without A Car

5. Marblehead, MA

Distance From Boston: 40-50 minutes.

Marblehead is an adorable little coastal town along the North Shore of Massachusetts, and a very quick road trip from Boston. This is the place to come if you’re looking for historical homes, small-town charm, great seafood, dramatic, rocky coastline and options for beaches.

Best Things To Do in Marblehead, MA:

• Marblehead Lighthouse & Chandler Hovey Park
• Self-guided historical home walking tour.
• Take in the views at Castle Hill Rock.
• For more information on the best things to do in Marblehead, click the link before for my detailed travel guide.

Click here to read even more awesome things to do in Marblehead!

6. Salem, MA

Distance From Boston: 30-40 minutes.

Salem is another little coastal town along the North Shore of Massachusetts, and is known for being the premier New England destination for all things spooky. While visiting Salem in October is definitely a bucket list-worthy goal, it’s actually a really wonderful town to visit all year round. It’s very walkable with a variety of things to do, and makes for a great day trip, or a weekend getaway.

Best Things To Do in Salem, MA:

• Winter Harbor Park and Lighthouse
• Salem Witch Trials Memorial
• Salem Maritimes National Historic Site
• Essex Street Pedestrian Mall
• House of Seven Gables
• Peabody Essex Museum

Psst! I have some helpful guides including planning the perfect Salem, MA day trip , and the best time to visit Salem if you need more information 😉

7. Rockport, MA

Distance From Boston: 50-60 minutes.

Rockport is one of my favorite coastal towns in all of New England. It has so much character, wonderful shops and restaurants, and really invites you to slow down a bit to take it all in. It’s a small town, and can be done in a day, but a weekend here would be a very relaxing road trip from Boston.

Best Things To Do in Rockport, MA:

• Visit Motif 1, the most painted building in New England, if not the country!
• Go for a scenic walk or hike at Halibut Point State Park.
• Meander through the shops on Bear Skin Neck.
• For more things to do in Rockport and the North Shore region, click the links below for my detailed travel guides.

Click here for more amazing things to do in Rockport!

Click here to read my travel guide on the best things to do on Cape Ann!

8. Newburyport, MA

Newburyport is a delightful little coastal town in Massachusetts that has a very traditional New England feel with beautiful homes at every turn, and an adorable little downtown area and waterfront park. Newburyport is also home to Plum Island, which is a gorgeous part of town with amazing beaches and wildlife sanctuaries.

Best Things To Do in Newburyport, MA:

• Visit Oldies Marketplace to look for antiques and treasures.
• Meander the streets of downtown to explore the beautiful storefronts.
• Take a leisurely stroll along the waterfront park.
• Pack a picnic or take a nature walk at Maudslay State Park , which has over 500 acres to explore.
• Head out on the open waters with Yankee Clipper Tours , and cruise around the Merrimack River and Newburyport Harbor.
• Drive over to Plum Island to visit Plums Island Beach, buy some handmade soaps at Plum Island Soap Co. , and walk the stunning nature trails at the Parker River National Wildlife Refugee .

Click here to read my full guide to visiting Newburyport & Plum Island!

9. Block Island, RI

Distance From Boston: 3-3.5 hours, which includes time to park at the ferry terminal, and ride the ferry.

Block Island is a beautiful island off the coast of Rhode Island with gorgeous beaches, walking trails, water activities, salt marshes, great restaurants and is overall a wonderful place to relax while appreciating the outdoors. This actually might be one of my top underdog suggestions for a weekend getaway from Boston.

It actually reminds me a bit of Prince Edward Island, so if you’re looking to live out your Anne of Green Gables dreams, but can’t make it to Canada, this is a great place to do that. There’s even a lovely hotel on the island called Avonlea.

To get to the island, you’ll need to drive to the Pt. Judith ferry terminal in Rhode Island. For more information on the ferry, click here .

Best Things To Do on Block Island, RI:

• Take in the views at Mohegan Bluffs.
• Rent a moped to explore the entire island.
• Spend some time swimming at Mansion Beach.
• Visit the island’s two lighthouses.
• Have lunch with a water view at The Oar .

Click here to read all my tips for taking a Block Island day trip!

10. Newport, RI

Distance From Boston: 1.5 hours, but always anticipate extra traffic crossing the Newport bridge.

Newport is a stunning coastal city in Rhode Island that’s the perfect destination for sailing, shopping, dining and being by the water. Even though it’s technically a city, I wanted to include it in the coastal destinations group because it definitely feels more like a resort waterfront town than a city.

With so many things to do, you could easily spend a weekend here, but Newport will also work for a day trip.

Best Things To Do in Newport, RI:

• Walk along Cliff Walk for amazing coastal views.
• Visit Bowen’s Wharf for shopping and dining.
• Grab a lobster roll at the Newport Lobster Shack .
• Walk over to Goat Island to see the lighthouse and take in views of the Newport Bridge.
• Sail around Narrangansett Bay with Sightsailing of Newport .
• Visit the unique shops along Thames Street.
• Grab lunch and cocktails at The Lawn at Castle Hill Inn , overlooking the water. Better yet, book an overnight stay for the ultimate Newport experience!

Click here to book your stay at The Castle Hill Inn in Newport .

Click here to read all my tips for taking a Newport, RI day trip!

Click here to read about all the best things to do in Newport, RI in the winter!

11. Mystic, CT

Distance From Boston: 1.5 hours

This adorable little town sits along Mystic River, and has an awesome mix of preserved maritimes history, small-town charm and nature. While Mystic is mostly visited for its quaint, waterfront downtown, it’s also home to parts of two bordering towns, Stonington and Groton, giving you opportunity to explore a few different coastal Connecticut destinations during your visit.

Best Things To Do in Mystic, CT:

• See penguins, beluga whales, sharks and sea lions at the Mystic Aquarium .
• Learn all about maritimes history at the Mystic Seaport Museum and Village , which is regarded as one of the best, if not the best, Maritimes museums in the country.
• Hit the trails at Bluff Point State Park.
• Take a sunset or moonlit cruise with Poet’s Lounge Sailing Charters .
• Grab a warm lobster roll, which originated in CT, at Ford’s Lobster in nearby Noank.

Click here to read about all the best things to do in Mystic, CT!

12. The Hamptons, NY

Distance From Boston: 5.5 hours if driving the whole way, 6 hours if you drive to New London, CT to take the ferry.

The Hamptons needs no introduction, as it’s become a famous summer destination in New York thanks to many celebrities calling it a secondary home. Sitting along the Long Island sound, you can expect gorgeous beaches, amazing shopping and restaurants, specialty food markets and farmer’s markets, wineries and plenty of opportunity for rest and relaxation.

The Best Things To Do in The Hamptons:

• Have a beach day and watch the surfers at Coopers Beach in Southampton.
• Go vineyard hopping, and taste some of the local wines. Channing Daughters Winery and Wölffer Estates are two great options.
• Take in the views at Montauk Lighthouse.
• Enjoy an afternoon of rest and restoration at the Montauk Salt Caves .
• Have some amazing and fresh seafood at Bostwick’s Chowder House in East Hampton.
• Rent a bike and ride along Gin Lane in Southampton for incredible views of the ocean, and to see some amazing houses.

13. Ogunquit, ME

Distance From Boston: 1 hour and 15 minutes

One of my favorite beach towns in all of New England is Ogunquit, which is one of the best places to visit in Maine in the summer , but it’s really fun in spring and fall, too. Offering both dramatic and rocky coastline that Maine is famous for, as well as a long, sandy beach that’s perfect for swimming, you’ll get the best of both worlds here. Ogunquit’s town is entirely walkable, so once you drive in, you’ll be able to leave your car behind and get almost everywhere by foot. There’s an amazing downtown scene with plenty of shops and restaurants, and you’re never that far from Ogunquit Beach.

Best Things To Do in Ogunquit, ME:

• Walk along Marginal Way, where you’ll get the most amazing views of the rocky coastline.
• Visit Perkins Cove to enjoy its charming shops and restaurants.
• Spend plenty of time at Ogunquit Beach, one of the best beaches in Maine.
• For more information on things to do in Ogunquit, click the link below for my detailed travel guide.

Click here to read about more amazing things to do in Ogunquit!

14. Kennebunkport, ME

Distance From Boston: 1 hour and 25 minutes

Just a short distance from Ogunquit is Kennebunkport, so these two destinations could easily be combined, and both are worth your time. Kennebunkport is full of character, and can be visited as either a day trip, or a weekend getaway, from Boston. Offering both beaches and a wonderful downtown scene, this is a great place to relax, unwind and enjoy being by the water.

Best Things To Do in Kennebunkport, ME:

• Visit Gooch’s Beach for a walk along the shore, or go for a swim.
• Have an authentic lobsterman experience with Rugosa Lobster Tours .
• Walk around the downtown and Dock Square shops.
• Grab an artisanal ice cream cone at Rococo Ice Cream .
• Have some craft cocktails and beer at Batson River Brewing and Distillery .
• Walk along Parson’s Way for amazing views of the dramatic coastline.
• Grab fresh seafood takeout from The Clam Shack .

Click here to see why Kennebunkport is one of the best Christmas towns in New England!

15. Bar Harbor/Acadia National Park

Distance From Boston: 4 hours and 45 minutes

One of the absolute best places to visit in all of Maine is Bar Harbor and Acadia National Park, and this will make an epic road trip from Boston. Bar Harbor is the adjacent town to Acadia, and where most people stay when visiting the park. Bar Harbor is a fun destination on its own because it’s full of character, and has great restaurants, and a beautiful harbor-side walking path and park.

Acadia National Park is one of the top destinations in all of New England, providing over 120 miles of hiking trails, and countless opportunities to take in some of the best and most incredible coastline views in the entire Northeast. In my opinion, this is one of the best roads trips from Boston you can take.

Best Things To Do in Bar Harbor & Acadia National Park:

• Walk along the Ocean Path trail inside Acadia, which is a flat, easy path along Shore Road that provides the most payoff for minimal effort when it comes to the most famous views in the park.
• Have lunch and popovers at Jordan Pond House inside Acadia, which offers views of the lawn and Jordan Pond.
• Drive to the summit of Cadillac Mountain inside Acadia for sunrise or sunset.
• Explore Bar Harbor’s downtown.
• Take a leisurely walk along Shore Path in Bar Harbor for the best views of the harbor.
• Visit Bass Harbor Lighthouse inside Acadia.

Tip : You’ll need to purchase a park pass to enter any attractions inside Acadia National Park. Park passes can be purchased online in advance by clicking here .

Psst! I have some posts on Acadia that you may find helpful, including my Acadia National Park Itinerary , and the Best Time To Visit Acadia National Park .

Luxury Road Trip Destinations From Boston

These destinations don’t have to be all about luxury, but since it’s nice to treat yourself every now and then, I wanted to include a few of my favorite luxury resorts that are easy road trips from Boston. If all you’re looking for is a little R&R and some serious pampering without having to leave the resort grounds, these are amazing places to visit.

16. Cliff House in Cape Neddick, ME

If you’re looking for the ultimate coastal Maine getaway to fully relax and recharge, then Cliff House will be the perfect road trip from Boston for you. This oceanfront resort sits atop 70 acres of cliffs, and offers incredible amenities that will allow you fully emerse yourself in Maine’s natural beauty without having to go far. Almost every square foot of this property has an ocean view, so there’s no way you can be stressed during your visit.

What To Expect During Your Stay At Cliff House:

• Beautifully-appointed rooms with a private terrace, and your choice of partial or full ocean views. Some rooms are also ocean-front.
• Complimentary coffee, tea and water stations on each floor.
• A full-service spa.
• Three oceanfront restaurants and a coffee cafe.
• Manicured gardens and pathways for relaxing walks.
• Two outdoor pools, two indoor pools and a hot tub.
• On-site shopping.

Click here to book your stay at Cliff House!

17. Ocean House in Westerly, RI

Distance From Boston: 1 hour and 45 minutes

For one of the very best luxury experiences in all of New England, Ocean House in Westerly, RI is a truly amazing destination. With the entire properly overlooking the Block Island Sound, it’s guaranteed you’ll be able to relax during your stay. Travel + Leisure has even named Ocean House as one of the top 100 hotels in the entire world.

What To Expect During Your Stay At Ocean House:

• Freshly designed and elegant coastal New England rooms and suites.
• Complimentary use of the hotels Mercedes-Benz convertibles for self-guided tours.
• Complimentary activities within the resort, such as daily yoga and cooking classes.
• Valet parking included in your room rate.
• Four on-site restaurants, and lobster dinners on the lawn during the summer.
• An on-site spa.
• Beautifully manicured lawns with yard games.
• Complimentary refreshments throughout the day.

Click here to book your stay at the Ocean House!

18. Mohonk Mountain House in New Paltz, NY

Distance From Boston: 3 hours and 45 minutes

If you’re looking for the ultimate road trip from Boston that combines hiking in the mountains with total relaxation, then Mohonk Mountain House is perfect for you. Located in the small college town of New Paltz, Mohonk Mountain House is right in the heart of the Hudson Valley of New York, and is surrounded by 40,000 acres of forest.

Overviews of the resort have been used in the Amazon Prime series Upload , and has long been rumored to be the inspiration behind Stephen King’s The Shining . But don’t let that scare you away! That only thing that will actually scare you once here is how amazing the views are.

If an overnight stay doesn’t work with your plans, guests can also purchase a day pass to the resort grounds, which allows you access to the hiking trails. This is a great way to enjoy the scenery without committing to an overnight stay.

What To Expect During Your Stay At Mohonk Mountain House:

• Traditionally-decorated rooms and suites that overlook the mountains. Most rooms also come with private balconies and rocking chairs.
• Lake Mohonk on the resort grounds.
• An all-inclusive stay where breakfast, lunch, afternoon tea and dinner, as well as all outdoor activities such as kayaks, row boats and canoes, are all included in the room rate.
• 85 miles of hiking trails right outside your door.
• Farm-to-table dining.
• Benches and chairs situated all over the resort grounds for moments of rest, and to clear your mind.

Click here to book your stay at Mohonk Mountain House!

Click here to read my detailed review of a Mohonk Mountain House Day Pass!

19. Mirbeau Spa in Rhinebeck, NY

Distance From Boston: 3 hours and 10 minutes

Mirbeau has a few locations throughout the Northeast, but my favorite of them all is in Rhinebeck, NY, a beautiful little town in the Hudson Valley. This particular Mirbeau Spa is one of the newer additions to their family, and is decorated in a modern, Parisian style, which makes it feel like a unique destination.

The spas at Mirbeau are really amazing. I’ve personally had massages and treatments at different locations, and they’ve always been consistent in quality (and, of course, relaxation). Guests are invited to walk around in robes, including at lunch, and the on-site hotel allows you to continue your relaxation journey into the evening for the perfect overnight stay.

What To Expect During Your Stay At Mirbeau in Rhinebeck, NY:

• A serene, calm spa atmosphere throughout the entire grounds.
• A relaxation room, aqua terrace and steam facility within the spa.
• Different spa packages to customize your stay that include dining options to make your visit stress-free.
• Luxurious and Parisian-inspired accommodations with options including in-room fireplaces and soaking tubs.

Click here to book your stay at Mirbeau in Rhinbeck!

Charming Small Town Road Trip Destinations From Boston

If you’re looking to visit some of the most charming towns in New England and New York for your road trip, I’ve got your covered! Here are the most adorable little towns to visit that make awesome road trips from Boston.

20. Saratoga Springs, NY

Distance From Boston: 3 hours and 15 minutes

While technically a city, Saratoga Springs’ historic downtown feels very much like a quaint village. Located in Upstate, NY and known for its horse racing track season, this destination has so much more to offer including a wonderful Main Street for shopping and dining, gorgeous parks, beautiful and historic architecture and live entertainment.

Best Things To Do in Saratoga Springs, NY:

• Walk around the grounds of Saratoga Spa State Park, which is a National Historic Landmark. You can enjoy a round of golf at an 18-hole championship course, have a picnic by the reflecting pool and admire the architecture of the Hall of Springs.
• July – Labor Day, visit the Race Track , and even try your hand at placing bets on the winner!
• Stroll through Congress Park, and find the mineral springs to taste the local water.
• Enjoy a healing bath at the Roosevelt Baths & Spa . The spa staff is trained on how to draw the perfect bath at just the right temperature, and the minerals in the waters have been said to have health benefits such as reducing sinus congestion and arthritis symptoms.
• Take in a live show at SPAC , one of the the country’s most renowned outdoor concert venues.
• Walk up and down Broadway, downtown’s main street, to visit the local shops and restaurants.
• Grab delicious cocktails with lunch or dinner at Morrissey’s Lounge & Bistro inside the famed Adelphi Hotel. Better yet, book an overnight stay at this Gilded Age-era boutique hotel, located in the heart of Saratoga’s downtown.

Click here to book your stay at the Adelphi Hotel in Saratoga Springs!

21. Skaneateles, NY

Distance From Boston: 5 hours and 20 minutes

Skaneateles is a lakeside town in the Finger Lakes region of Upstate, NY, and is a wonderful place to visit, especially in the Summer. With Skaneateles Lake right in the heart of downtown, and an adorable Main Street with really nice shops and restaurants, the quaintness of the town is perfect for rest and relaxation, but also offers plenty to do to keep from ever being bored.

Best Things To Do in Skaneateles, NY:

• Walk around Main Street to visit the boutiques.
• Sit and admire the views of the lake from the town’s many waterfront areas.
• Visit Anyela’s Vineyards to enjoy a tasting, or sip on a glass of wine and take in the peaceful views of the vineyards.
• Head out onto the lake for a boat tour.
• Grab dinner and drinks at the Sherwood Inn , located right in the heart of town, and just across the street from the lake.
• Spend the day getting pampered at Mirbeau Inn & Spa , the original Mirbeau location, which is home to a Monet-inspired garden and bridge.

Click here to book your stay at Mirbeau Inn & Spa in Skaneateles!

Click here to read more suggestions on the best things to do in Skaneateles, NY!

22. Lake Placid, NY

Distance From Boston: 5 hours

Known for hosting two Olympic games, Lake Placid in the Adirondack region of Upstate NY has so much more to offer (although, the Olympic sites are definitely worth visiting!). I personally love visiting Lake Placid in the winter because the alpine-inspired town really seems to come alive with apres-ski vibes, but it’s really a great destination all year round. While in Lake Placid, you’ll be surrounded by mountains and fresh air, and feel like you’ve truly escaped from every day life.

Best Things To Do in Lake Placid, NY:

• Walk around Mirror Lake, located in the heart of Lake Placid’s downtown.
• In the winter, enjoy skiing at Whiteface Mountain , and ice skating and a Toboggan Chute on Mirror Lake.
• Enjoy the miles of hiking trails in the nearby mountains.
• Walk around the alpine-inspired downtown village to visit the quaint shops.
• In the summer, go for a swim in Mirror Lake from the public beach area.
• Visit the Olympic sites, including the ski jump, ice arena and the Lake Placid Olympic Museum .
• Walk around High Falls Gorge, a 22-acre nature park with waterfalls.
• Grab drinks and lunch or dinner at The Cottage, a restaurant at Mirror Lake Inn Resort & Spa that sits right on Mirror Lake. Better yet, book an overnight stay, and also enjoy the on-site spa for the ultimate Lake Placid getaway!

Click here to book your stay at the Mirror Lake Inn Resort & Spa in Lake Placid .

Click here to read my post on all the best things to do in Lake Placid in the fall!

23. Hudson, NY

Distance From Boston: 2 hours and 45 minutes

Located in the Hudson Valley of New York, Hudson is known as being incredibly charming, and one of the best destinations for antiquing in the area. This is a great little town to visit if you’re looking to relax, enjoy a small-town atmosphere and see where the day takes you. Hudson is also a great destination if you’re looking to explore the entire Hudson Valley region.

Best Things To Do in Hudson, NY:

• Antiquing! There are countless antique shops in Hudson, and you’ll definitely want to check out The Antique Warehouse , which has over 300,000 sq. feet of treasures.
• Stroll down Warren Street, where most of the storefronts can be found.
• Take a boat cruise along the Hudson River with Hudson Cruises , which offers tours to the Hudson-Athens Lighthouse, and even murder mystery cruises!
• The Hudson Farmer’s Market is regarded as one of the best in the region, and is open every Saturday in-season, and also has a winter location February-April.
• Tour the local art galleries.
• Go for a nature walk in the Greenport Conservation Area, which is home to over 7 miles of trails, and is walkable from downtown Hudson.

Click here to read my post on the best things to do in Upstate New York in the fall!

24. Manchester, VT

This small little town in Southern Vermont is the perfect place to disconnect and relax. As you cross the New York/Vermont border, you’ll begin to see the tall mountains all around you, and instantly feel more at peace. In fact, you’ll be able to see the surrounding mountains from everywhere in downtown Manchester. And with everything to do from shopping and dining to hiking and nature walks, you’re sure to find something that everyone in your group will enjoy.

Best Things To Do in Manchester, VT:

• Hike or drive up Mt. Equinox, the tallest mountain in the Taconic Range, and enjoy the incredible views from above.
• Browse through Northshire Bookstore , an amazing independent bookstore that’s been in business since 1976. Here, you’ll find new and used books, a wonderful children’s section, and unique Vermont-inspired gifts and souvenirs.
• Visit Hildene , the Lincoln family estate, where visitors can tour the gardens, walking trails, farm land and indoor exhibits, and enjoy sweeping views of the Vermont countryside.
• Rent a tube at Vermont River Runners and take a relaxing water tube ride along the Battenkill River, which is perfect for a warm summer day.
• Grab a sandwich as big as your head at Zoey’s Deli . I also love their homemade chips!
• Hike the Lye Brook Falls trails to visit a beautiful waterfall. The trailhead is a short 5-minute drive from town center.
• Go for a dip in the Dorset Marble Quarry for a unique swimming experience!
• After your swim, visit the Dorset Union Store , a quintessential Vermont country store.

Click here for an awesome Vermont covered bridges tour itinerary!

25. Woodstock, VT

Distance From Boston: 2.5 hours

Of all the Vermont towns on this list, I think Woodstock might be my favorite. I love them all, but there’s something about Woodstock that just screams New England charm, and perfectly balances being a town that caters to tourists, while not losing any of the local character. It’s one of those idyllic towns you’ll daydream about moving to.

Best Things To Do in Woodstock, VT:

• Walk through the truly adorable village and enjoy the local shops and coffee cafes.
• Head over to the Woodstock Middle Covered Bridge, located right in the village, for a picture-perfect Vermont moment.
• Get your hands muddy with a pottery workshop at Farmhouse Pottery .
• Drive to nearby Quechee and visit the Simon Pearce Restaurant & Mill , and take in a live glass-blowing demonstration, as well as lunch overlooking the gorge.
• Head over to Quechee Gorge Village after Simon Pearce for some antiquing.
• Visit Billings Farm & Museum to tour a working dairy farm, gardens and orchards, and see live demonstrations. The grounds here are truly spectacular!
• Hike Mount Tom for stunning views of Woodstock from above.
• Best Places To Stay In Vermont In The Fall
• Best Things To Do In Woodstock, VT
• Best Winter Getaways In New England

26. Stowe, VT

Distance From Boston: 3 hours and 20 minutes

Stowe is an adorable little village in Northern Vermont that I love to visit, and it always puts a smile on my face. Even though it’s a well-known ski destination in the winter months, it’s a great little place to visit year-round will lots of outdoor activities and perfect Vermont scenery all over, including some beautiful covered bridges.

Best Things To Do in Stowe, VT:

• Hike Mount Mansfield, the highest mountain in Vermont, or drive the auto road to the summit.
• See if you believe in ghosts at Emily’s Covered Bridge. Legend says it’s haunted by a girl who hung herself on the bridge after her boyfriend never came to meet her.
• Walk the Stowe Recreation Path, a 5.5-mile long paved path that goes through beautiful scenery throughout the village. The path can be accessed from several locations in the village.
• Connect to the Quiet Path along the Rec Path, which is reserved for walkers only (meaning, no bikes wizzing by you). It meanders through parts of Mayo Farm, and is a very relaxing way to spend an afternoon.
• Go hiking at Smuggler’s Notch State Park.
• Visit the nearby Ben & Jerry’s Factory for a tour.
• Explore Sterling Falls Gorge.
• In the winter, hit the slopes at Stowe Mountain Ski Resort.
• Pick up some chocolates from Lake Champlain Chocolates.
• Best Things To Do In Stowe, VT
• Best Stops To Make When Driving From Boston to Stowe, VT
• Best Things To Do In Vermont In The Winter

27. Greenwich, CT

Distance From Boston: 3 hours

Greenwich is an absolutely beautiful town that sits right on the border of New York, and also very accessible to Manhattan. I love coming to this idyllic little town when I want a day of relaxing, shopping, dining, being outside, visiting the beach and enjoying the gorgeous scenery.

Best Things To Do in Greenwich, CT:

• Shop the stores along Greenwich Avenue.
• Enjoy a serene walk through the Donald M. Kendall Sculpture Gardens in nearby Purchase, NY.
• Meander through Montgomery Pinetum, a public park that’s very relaxing, and also has beautiful ponds, nature trails and gardens with an educational center and greenhouse.
• Head to the Lobster Bin for an amazing lobster roll on-the-go.
• Spend some time at the beaches along Greenwich Point Park.
• Admire the architecture of the historic district buildings.

28. Jackson, NH

Let’s head to the White Mountain National Forest in New Hampshire! One of the best towns to stay in is Jackson, where you’ll find a lovely downtown and Main Street, an iconic red covered bridge, and endless opportunities to explore the White Mountains region, including lots of hiking and outdoor activities. While it’s most popular during the winter for skiing, and the fall for foliage season, Jackson can be enjoyed year-round.

Best Things To Do in Jackson, NH:

• Visit Honeymoon Bridge, the town’s famous red covered bridge.
• Drive to the summit of Mount Washington, the highest peak in New England.
• Hike the Glen Ellis Falls Trail.
• Explore the downtown shops and restaurants.
• In the winter, go skiing at Black Mountain. In the summer, the mountain offers horseback riding and lots of hiking trails.

You may also like: The best things to do in New England in the fall!

City Life Road Trip Destinations From Boston

Even though you’re road-tripping from a city already, it’s still exciting to explore a new one. There are quite a few cities that make for amazing road trips from Boston, and many of them can be combined with other destinations from this list to offer the best of city life, and coastal or small-town living.

29. Portsmouth, NH

Distance From Boston: 1 hour

This charming little city is just a short drive from Boston, and definitely feels more like a town than a city. Portsmouth is a port-side city with a gorgeous downtown filled with quaint shops and boutiques, and is known as being a huge foodie destination. This is a great city to visit if you’re looking for a lot of character, and lots of options when it comes to being outside, dining and shopping.

Best Things To Do in Portsmouth, NH:

• Grab some fresh and delicious pastries from Elephantine Bakery , and be sure to enjoy them just outside the cafe in the most adorable little courtyard.
• Shop the boutiques in downtown Portsmouth.
• Walk along Prescott Park, which has over 10 acres of waterfront gardens and paths, and is home to live entertainment in the summer months.
• Take a dip in the water at Great Island Common Park.
• Go brewery hopping, as Portsmouth is home to five breweries.
• Enjoy a drink at the Book & Bar , a combined bookstore, cafe and bar.
• Head out onto the water with Portsmouth Harbor Cruises .
• Visit Portsmouth Harbor Lighthouse.

30. Providence, RI

Providence is the capital of Rhode Island, and also home to famed schools Brown University and the Rhode Island School of Design. It’s also a really fun city to be a tourist! With Providence River running through the city, you still have opportunities to feel like you’re connected to nature, and with tons of restaurants, shops, nightlife and history, this destination makes for an amazing road trip from Boston.

Best Things To Do in Providence, RI:

• Visit The Arcade , the country’s very first shopping mall designed with Greek revival architecture, and now home to some awesome boutiques and art galleries.
• Visit the Roger Williams Park Zoo , which is the third oldest zoo in the country, where guests can feed giraffes and other farm animals, and see over 160 different species while visiting. You can also jump on the Explore and Soar ride, which is a fun zip ride and train excursion through the forests.
• Enjoy a leisurely walk along the Providence Riverwalk.
• During the summer, experience WaterFire, where braziers are set with bonfires in the middle of the river.
• Take in the exhibits at the RISD Museum of Art.
• Take a Venetian gondola ride along the river at Waterplace Park.
• Do a self-guided historical walking tour along Benefit Street to see some of the city’s most historic houses and buildings.
• Take a boat tour along the Providence River.

Click here to read my post on the best day trips from Providence!

31. Portland, ME

Portland is an exciting waterfront city in Maine that sits on a peninsula along Casco Bay, and provides the best of both worlds as far as being a city destination that’s also coastal. With things to do outdoors along the dramatic coastline, to an amazing restaurant and food scene, Portland has a little something for everyone during your road trip from Boston.

Best Things To Do in Portland, ME:

• Portland Head Lighthouse is a must! It’s the most famous lighthouse in Maine, and one of the most iconic in all of New England. Nearby, you can also visit Spring Point Ledge Light and Bug Light, and do a mini lighthouse tour without leaving the city!
• Visit one of my favorite breweries in New England, Bissell Brothers . They also get bonus points for being close to the waterfront at Thompson’s Point.
• Meander around Old Port to see the city’s fishing industry come to life.
• Walk along the lively waterfront scene on Commercial Street for shopping, dining and water views.
• Tour the open waters on a beautiful Schooner tour with Portland Schooner . They also invite you to pack a picnic with beer and wine to enhance your experience.
• Tour the Portland Arts District, which is filled with art galleries, museums and theaters.
• Take a culinary tour of the city and learn the very best places to eat, led by a local. Click the link below to book your tour, or learn more info.

Click here to book your walking culinary tour in Portland!

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32. New York City

Distance From Boston: 3 hours and 45 minutes (but always allow extra time for traffic)

New York City needs no introduction, and if you’ve never been to the city that never sleeps, this is an absolute must if you’re looking into road trips from Boston. Below is a list of my absolute favorite things to do when I visit NYC, which includes the best things to do for first-time visitors.

The Best Things To Do in New York City:

• Walk the Brooklyn Bridge and visit DUMBO for sweeping views of both the Brooklyn and Manhattan bridges.
• Get bagels at Brooklyn Bagel (the best in the city).
• Visit Central park, and be sure to stop at Bow Bridge, Belvedere Castle and The Mall walkway.
• Grab a slice of pizza at Joe’s (150 E 14th St.)
• Explore the MET Museum and Cloisters.
• Take the Staten Island Ferry for views of the Statue of Liberty (this is free and way better than the official tours, which are super crowded!).
• See a broadway show.
• It’s touristy, but I love going to the top of the Empire State Building.
• Walk around the West Village for amazing streets and brownstones.

33. Burlington, VT

Burlington is a small and beautiful city in Northern Vermont that sits along Lake Champlain, and is wonderfully diverse, exuberant and also very relaxing. This is a great destination if you’re looking for a small-town feel set in a bigger city, waterfront and outdoor activities, an art scene and plenty of amazing restaurants.

Best Things To Do in Burlington, VT:

• Walk around Church Street, a pedestrian-only area lined with unique shops and restaurants.
• Stroll around the waterfront to admire the views of Lake Champlain, as well as the Burlington Breakwater Lighthouse.
• Bike the Burlington Bike Path, a beautiful path along the lake that’s over 7 miles long.
• Go kayaking or stand up paddleboarding on the lake.
• Head to nearby Shelburne to tour Shelburne Farms , one of my favorite things to do in all of Vermont! There are tons of hiking and walking trails through the 1400-acre picturesque grounds, and you can stop to sample their homemade cheeses and baked goods along the way.
• Take in the art scene on the South End, which is loaded with galleries and shops.
• Get a taste for the local brews with a Sip of Burlington Beer Tour. Join a small group for dinner, and learn from a local brew expert as you taste all the different beers that are brewed nearby. Click the link below to learn more, or book your tour.

Click here to book your Beer of Burlington experience!

34. Philadelphia, PA

Last but most definitely not least on our round-up of the best road trips from Boston, is the city of Brothery Love, Philadelphia. Philly is Pennsylvania’s largest city, and is deeply rooted in history, but there are all kinds of things to do from exciting nightlife and amazing food to parks and waterfront activities.

Best Things To Do in Philadelphia, PA:

• Run up the Rocky Steps at the Philadelphia Museum of Art, and snap a picture with the Rocky statue. A bit touristy, but if you’re a fan of the movie, you gotta go for it.
• Speaking of the Philadelphia Museum of Art , after your Rocky moment, be sure to visit. They have an amazing American art collection, as well as works by famed impressionists Renoir, Degas and Monet.
• Tour Independence Hall, regarded as the birthplace of the United States, and where the Declaration of Independence was debated by our Founding Fathers.
• Venture just outside the city to visit Longwood Gardens, an expansive garden oasis filled with both indoor and outdoor gardens and, and beautifully designed grounds.
• Grab a Philly cheesesteak at Woodrow’s Sandwich Shop .
• Stroll along the Delaware Riverfront to explore Cherry Street and Race Street Piers, and take in amazing views of the Benjamin Franklin Bridge.
• Hop on a BYOB trolley tour of the city, hosted by hilarious guides that share historic and entertaining information, and take you to some of the top sites in the city. Click the link below to learn more, or book your tour.

Click here to book your Historically Hilarious Trolley Tour in Philadelphia!

Road Trip Itinerary Options

If you’re looking to combine towns from this list into longer roads trips, or are wondering which towns are close enough to combine together to maximize your time and cover the most ground, I’ve got you covered! Below you’ll find suggested itineraries with different routes you can take while planning the best road trips from Boston.

Option 1: Massachusetts North Shore Road Trip From Boston

For this route, you’ll head north from Boston and visit the following destinations:

• Newburyport & Plum Island
• Portsmouth, NH

Days Needed For This Route: 2-4 . If you’re looking for an easy road trip from Boston with lots of options, this is an awesome route to take. You can do it in as little as 2 days for a weekend trip, or add on two additional days to take your time and explore each town.

Option 2: Cape Cod & The Islands Road Trip From Boston

For this route, you’ll head south from Boston and visit the following destinations:

• Martha’s Vineyard

Days Needed For This Route: 7-8 days. Because this route requires ferries from Cape Cod to the islands, and with Cape Cod being a larger region to explore, I recommend a week.

If you have less time, the islands could be done as day trips, and you could attempt this route in about 5 days . If you have 10 days, I would suggest spending one night in Plymouth, 5 days on Cape Cod, two nights on Nantucket and two nights on Martha’s Vineyard for the ultimate Cape Cod road trip.

Option 3: Boston To Bar Harbor Road Trip

This route will take you up the coast of Maine and stop in these destinations:

• Newburyport, MA
• Ogunquit, ME
• Kennebunkport, ME
• Portland, ME
• Bar Harbor, ME

Days Needed For This Route: 7-10 days. I suggest this much time because your final destination, Bar Harbor, is home to Acadia National Park, and there’s so much to see and do just in the park. And each stop along the way is a very worthy destination to spend at least one night in.

If you’re very short on time, you can do this route in 4 nights with this itinerary:

• On your way to Ogunquit, pass through Newburyport and spend 2-3 hours there. Arrive in Ogunquit late afternoon to spend the night.
• The next day, spend the morning in Ogunquit, and then drive to Kennebunkport to spend about 3 hours exploring there. Drive to Portland, and spend the night.
• The next day, spend your morning in Portland, and then drive to Bar Harbor to arrive by mid-afternoon. Spend 2 nights in Bar Harbor.
• Drive back to Boston.

I have a detailed Boston To Bar Harbor, Maine Road Trip Itinerary if you’d like more help with planning!

Option 4: Vermont Road Trip From Boston

For this route, you’ll head northwest of Boston, and drive through the best towns in Vermont from this list. You’ll cover these destinations:

• Manchester, VT
• Woodstock, VT
• Burlington, VT

Note : This route isn’t as direct as the other routes, and will include 6.5 hours of driving time to get from Boston to Burlington, stopping at the other destinations along the way. But then you can drive direct from Burlington to Boston on your way home, which will only take 3.5 hours.

Days Needed For This Route: 3-5 days . This could easily be a long weekend itinerary if you don’t stop in each town overnight, and just visit Manchester and Stowe for a few hours each. You could, of course, take your time, and do up to 5 nights for this itinerary.

Option 5: Rhode Island & Coastal Connecticut Road Trip From Boston

This route will take you southwest from Boston, and you’ll visit these destinations:

• Providence, RI
• Newport, RI
• Block Island, RI
• Westerly, RI

Days Needed For This Route: 3-6 days . This is another itinerary you could also do in a weekend if you only spend a few hours in Mystic, as a day trip from Newport, and skip going to Block Island. To visit all these destinations, you’ll need about 5 days, but 6 would be ideal to not feel rushed.

Tip : If you wanted to extend your road trip further along this route, there is a ferry that leaves from New London, CT, and goes to the Hamptons!

Option 6: Boston To New York City & The Hamptons Road Trip

This route will take you to these destinations:

• Rhinebeck, NY
• New Paltz, NY
• New York City
• The Hamptons
• Optional add-on: Philadelphia, PA

Note : The route from Boston to The Hamptons, while making all the stops in the Hudson Valley in-between, is not direct, and will take about 7.5 hours without stops, so I highly suggest you stop overnight in at least one of the towns to break up your drive. If you wanted to visit Philadelphia, this would be the route you would want to add that destination to, as you will have to drive through NYC to get there.

Days Needed For This Route: 1 week. To do this route in 7 days, I would suggest spending a few hours each in Hudson and Rhinebeck, then spend the night in New Paltz (splurging at Mohonk Mountain House is definitely worth it!). Then drive to NYC the next day, and spend 3 nights there. Then drive to The Hamptons, and spend 3 nights. If you want to add Philadelphia, you’ll want to add an extra night or two.

If you’re short on time and want to do this route in fewer days, I would suggest spending a night in the Hudson Valley (same as above), spend 3 nights in NYC, but include a day trip to The Hamptons. Or, if The Hamptons is of more interest to you, you could spend one night in NYC, and spend a night or two in The Hamptons. And then drive back to Boston.

The other option is to drive direct from Boston to New York City, and leave out the Hudson Valley towns entirely. On that route, your focus would be New York City and The Hamptons.

What Towns Are 1 Hour From Boston?

Plymouth, Salem, Rockport, Newburyport are all within an hour from Boston, and make for wonderful road trips or day trips from Boston.

Towns not mentioned on this list that are also an hour or less from Boston that are perfect for a road trip are Scituate, Gloucester, Manchester-By-The-Sea and Essex, all of which are located in Massachusetts.

What Cities Are 6 Hours From Boston?

New York City, Portsmouth, NH, Philadelphia, PA, Portland, ME, Burlington, VT and Providence, RI are all within 6 hours or less from Boston, and are all included on this list as amazing road trips from Boston.

Is Boston Close To Niagara Falls?

Boston is over 7 hours from Niagara Falls, and for that reason, didn’t make this list of road trips. But if you have extra time, it could be added to a road trip itinerary for Skaneateles, NY and the finger lakes region.

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That’s A Wrap On The Best Road Trips From Boston

As you can see, Boston is really an incredible gateway to all of the Northeast, making it easy to take lots of different road trips. Whether you want to explore the coast of Massachusetts and Maine, go cute-town-hopping through Vermont or visit as many cities as you can, you’re now ready to plan which of these road trips from Boston is perfect for you.

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Best Road Trips From Boston

Top road trip destinations from boston.

No matter what time of the year you visit Niagara Falls, you will fall in love with its majestic scenery. If you travel during the warmer months, you can take a boat tour to see the raw power of nature up close and can extend your trip to see the falls from the Canadian side.

If one city has something unforgettable for every type of traveler, it is the Big Apple. Spend some time at Times Square, explore world-class museums, enjoy Broadway shows, and make sure to book a table at one of the many famous restaurants in the city.

Portland is a coastal gem known for its lighthouse-dotted landscapes and up-and-coming food scene. From strolling along the cobblestone streets of the Old Port to treating yourself to fresh seafood and craft beer, Portland is the quintessential New England town.

Acadia National Park is one of the most-visited parks in the country and it is easy to understand why. Hike granite peaks, bike historic carriage roads, and witness sunrise at Cadillac Mountain where the mountains meet the sea.

A visit to Washington DC, is a must for any history buff. Here, you can tick iconic landmarks off your bucket list, such as the Lincoln Memorial, the Smithsonian Museums, and the White House. The city is also home to some incredible Michelin-rated restaurants.

Cape Cod and its eclectic outermost town, Provincetown, are amazing summer destinations. Known for its stunning beaches, historic lighthouses, and buzzing arts scene, this picturesque peninsula is also a great place to enjoy whale watching from mid-April to October.

If you have spent some time in the US, it is likely that you are familiar with the Liberty Bell and Independence Hall in Philadelphia. Come here for history, and you will end up staying for the eclectic neighborhoods and the famous Philly cheesesteak!

If you are looking for the perfect blend of historic charm and modern sophistication, Providence is the perfect destination from Boston. Make sure to enjoy a scenic walk around the WaterFire art installation, and delve deeper into the history of one of America's oldest cities.

For a slice of Europe in North America, Quebec City is a UNESCO World Heritage site famous for its fortified colonial core and stunning Château Frontenac. Here you will enjoy the French heritage of the city, its delicious cuisine, and festive events year-round.

Discover Toronto, Canada's largest city! From its easily recognizable CN Tower to its bustling markets, expansive green spaces, and waterfront districts, you will find plenty to do in this charming city, which blends urban fun and that cozy neighborhood feeling perfectly.

There is nothing quite like a cross-country adventure, and all the miles you will have to cover to reach LA will be worth it! Famous for its iconic Hollywood Sign, always-busy Venice Beach, and glamorous Rodeo Drive, Los Angeles is one of the best destinations on the Pacific Coast.

Orlando is world-famous for its theme parks and attractions. From the magic of Walt Disney World to the popular rides of Universal Studios, Orlando offers endless fun for families and visitors of all ages. The city is home to many beautiful parks, too, if theme parks aren't your thing!

Soak up the sun in Miami, a city famous for its stunning beaches, and glitzy nightlife. During the daytime, you can enjoy a tour to view the Art Deco buildings of South Beach or escape to the wild landscapes of the Everglades. The Magic City has something for everyone.

You will immediately recognize the famous Chicago skyline as you approach the Windy City, full of Midwest charm. Dive into the city's jazz and blues scene, savor deep-dish pizza, and visit iconic sites like Millennium Park and the Art Institute of Chicago.

A relatively manageable drive across the Canadian border and you will find yourself in Montreal, home to the historic streets of Old Montreal and Mount Royal Park, which features stunning views of the city and snowshoeing, tubing and skating in winter!

Nova Scotia is located where the Atlantic Ocean meets rugged coastlines and jaw-droppingly beautiful landscapes. Another destination where you can admire historic lighthouses, indulge in fresh seafood, and experience the warm hospitality of the Canadian Maritimes.

Head to Myrtle Beach for a fun-filled getaway in the heart of the Grand Strand. Enjoy miles of sandy beaches, amusement parks, and live entertainment. This family-friendly destination offers something for everyone, from golfing and shopping to dining and nightlife.

Raleigh is the capital of North Carolina, known for its pretty parks, and historic sites. When in Raleigh, we recommend visiting the North Carolina Museum of Natural Sciences, strolling through the beautiful Pullen Park, and enjoying the city's growing culinary scene.

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7 Spectacular Weekend Road Trips from Boston, Massachusetts

Posted by Sarah Lamagna May 25, 2021 Updated April 11, 2023

Tired of the cobblestone streets and “R’s” left out of every word? Luckily for the residents of Boston, there are some epic weekend road trips within a few hours of the city.

Boston might be home to some incredible sights and truly dedicated sports fans, but sometimes a weekend away is just what the doctor ordered.

Whether you’re looking for gorgeous coastal villages, quaint mountain towns, some good ol’ fashioned Ben & Jerry’s ice cream, or views from the top of Mount Washington, we’ve got what you need.

Related Read:   10 Chill Romantic Getaways in Massachusetts

Road Trip Planning

Before you head out, make sure to plan accordingly. Unlike a lot of other places across the country, weather and traffic are fairly predictable in and around Boston. There usually aren’t “surprise” storms and traffic is, well, always there.

Expect typical weather patterns during corresponding seasons: it snows in the winter, rains in the spring and fall, and is hot/humid in the summer. You won’t need any special car enhancements (like four-wheel drive) to get to any of the places on this list. But beware of potholes – they are a’plenty in the northeast. Construction crews never seem to be able to keep up with them.

Speaking of construction; it’s constant in New England and especially in Boston. Construction crews are out in freezing temperatures and rainy days. Expect traffic to be slower and heavier in these areas. It’s also important to note that depending on your destination from Boston, you might pass through several rush hours.

There’s also a reason that Boston drivers are well-known across the country; they are aggressive. Come prepared knowing that if you stall too long when a red light turns green, you will definitely be beeped at – car horns are the state bird call of Massachusetts…just kidding.

Pro tip: do NOT dilly dally in the passing lane. This is a huge pet peeve of most New Englanders. If you aren’t passing someone, get out of that lane.

Related Read: 5 Best Day Trips From Boston for Scenic New England Getaways

7 Amazing Weekend Trips from Boston

1. north conway, nh.

This picturesque town has everything you’ll need for outdoor adventure. North Conway is in the heart of White Mountain National Forest which prides itself in a myriad of outdoor activities including hiking, biking, skiing, and fishing (among others).

Mount Washington looms in the distance as if beckoning you to climb it. At 6,288’ above sea level, Mount Washington is the tallest mountain in the northeast. You can climb it anytime of year (although we recommend a guide service like Nemo Mountaineering in the winter) through several routes, with the Tuckerman Ravine route being the most popular. You can also drive up yourself during the late spring/summer months or take the Cog Railway .

The heights around Mount Washington aren’t for everyone, though. Instead, you can take a drive along the Kancamagus Highway (the Kanc to locals). It can get busy on the weekends, especially during peak leaf-peeping season in the autumn.

You can also simply hang around town: visit Zeb’s General Store , grab brunch at Peach’s Restaurant , drink a beer at Moat Mountain Smokehouse and Brewing , or visit the Conway Scenic Railroad .

• Distance from Boston : 137 miles
• Drive time: 2 hours, 30 minutes

2. Westerly, RI

Head on down to this southern Rhode Island beach town to catch some waves and rays (and maybe a glimpse of TSwift ). It’s the shortest trip on our list from Boston which means extra time to soak in the sun and get that tan you’ve been yearning for.

The best place for getting in that vitamin D is at Watch Hill . It’s great for kids and adults alike and includes a Merry-Go-Round where kids can take their chances grabbing brass rings for a shot at a free ride – psst…make sure to grab an outside horse to do this.

Aside from beaches, there’s plenty of other things to do including popping your head into a few boutiques like Anther Living and Rochelle’s . For some good food (or a great place to stay), check out Ocean House’s many culinary journeys including a taco shack, a secret garden creperie, and a raw bar – among so much more.

• Distance from Boston : 92 miles
• Drive time: 1 hour, 30 minutes

3. North Adams, MA

Grab a wand and your spell book to head to the place that inspired writers like J.K. Rowling, Henry David Thoreau, and Herman Melville. Located in northwestern Massachusetts, North Adams is in the heart of the Berkshire Mountains.

You can head up to the top of the state to visit Mount Greylock and the Massachusetts War Memorial Tower. On a clear day, you can see for 70 miles in either direction into five states.

Too bad you didn’t really know magic, though, and get yourself back down to town quickly. Whenever you do, head over to PUBLIC for some great eats and then to Bright Ideas Brewing for the best brewery in town.

• Distance from Boston : 136 miles
• Drive time: 2 hours, 45 minutes

Related Read: 10 of the Best Airbnbs in Boston, Massachusetts

4. Lake George, NY

If you’re in the mood for some lake-living, then Lake George is your answer. It’s full of every type of water-related activity you can think of: boating, kayaking, water skiing, canoeing, fishing, and even hopping on a cruise . But if water isn’t your thing, well, maybe go elsewhere?

Seriously, though, on top of every water sport in the world, Lake George has many land activities. For the most unique experience on land, though, consider taking a rail bike tour through the Adirondacks. Or you could check out the Natural Stone Bridge and Caves , which is home to the largest marble cave entrance in the eastern United States.

• Distance from Boston : 227 miles
• Drive time: 3 hours, 30 minutes

5. Mystic, CT

Move over Leonardo Dicaprio, Mystic is the true home of the hero of the Titanic. That is, Bob Ballard who discovered the famous ship wreckage. He founded the Institute for Exploration which partnered with the Mystic Aquarium – located in, you guessed it, Mystic.

But this quaint, coastal town is more than marine ecosystems. You can travel back in time and visit Mystic Seaport Village and set foot on a veteran training ship . If you need to pick up some trinkets for your family or friends, head to Franklin’s General Store in Olde Mystick Village . Grab a pizza slice from famed Mystic Pizza (yup, it’s the same one in the movie starring Julia Roberts). To wind down for the evening, get a scoop of ice cream from Mystic Drawbridge Ice Cream and watch the boats head down the Mystic River.

• Distance from Boston : 100 miles
• Drive time: 1 hour, 40 minutes

Related Read:   The 6 Best Scenic Byways to Fully Experience Massachusetts

6. Stowe, VT

No matter the time of year you visit this northern Vermont town, Stowe is perfect for any traveler. Into skiing? Head to Stowe Mountain Resort . Rather have a spa day? Then Stoweflake is your destination. Or maybe you just want some ice cream? Then take a tour of the hippie owners’ flagship Ben & Jerry’s store in Waterbury (just south of Stowe).

A trip to Stowe isn’t a trip, though, until you visit the Trapp Family Lodge . You can stay there the entire weekend, grab a beer from the von Trapp Brewery , or experience one of the many activities there including disc golf, biking, hiking, and carriage rides.

Pro tip: don your best dirndl or lederhosen during their Oktoberfest . It’s a heck of a time!

• Distance from Boston : 199 miles
• Drive time: 3 hours

7. Kennebunkport, ME

Kennebunkport is THE quintessential New England coastal town. To get a real feel for its personality, head on out to Dock Square where you can peruse art and buy some fashionable clothing at the boutique shops or sit in one of the many cafes along the main drag.

Get your lobster fix at Port Lobster or Mabel’s (they’re both favorites for the locals) or try the famed Whoopie Pie found at HB Provisions . For adventurous souls, visit the Rachel Carson National Wildlife Refuge or kayak around Cape Porpoise Pier . End your day by resting your head (or simply walking around the 60 acres of lush gardens) at St. Anthony’s Monastery and Franciscan Guest House .

• Distance from Denver : 84 miles

Explore New England

12 Magical Glamping Destinations in New England

10 Best Massachusetts Airbnbs for a Unique Weekend Getaway

15 Best Hiking Trails Near Boston, Massachusetts

12 Best VRBOs in Maine for a Unique Vacationland Getaway

10 Super & Secluded Maine Cabin Rentals

10 of the Best Airbnbs on Cape Cod, Massachusetts

8 Unique Places to Stay Near Boston When You Need to Get Away

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Seen in: Massachusetts , New England , Road Trips

Posted by Sarah Lamagna

Sarah is an ecologist-turned-freelance writer specializing in the ecotourism and slow/sustainable travel industry. Her bylines include The Denver Post, 5280 magazine, VeryWellFamily, Matador Network, and was an expert on NPR’s The Takeaway for her work on the wildfires in Colorado.

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5 charming New England towns you can drive to from Boston

Update: Some offers mentioned below are no longer available. View the current offers here .

While a typical summer weekend in Boston usually means a stroll along the Charles River or a picnic in the Common, we all know this summer won't be anything close to normal.

Travelers who need a change of scenery can find charming New England towns and untouched stretches of wilderness just a few hours from the city.

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From Boston , travelers can reach many exciting and overlooked destinations, such as the vertical granite cliffs of Camden Hills State Park and historic towns filled with lovely Victorian homes. If you're planning on spending more time in the great outdoors than ever before, there are plenty of opportunities for adventure-fueled days spent rock-climbing, hiking and kayaking.

Related: 6 of the best-value points hotels in Boston

Whether you're planning a road trip from Boston this summer or a year from now, remember that small New England towns are filled with intimate B&Bs and historic inns, be sure to book with a credit card that will help you maximize your travel purchases, such as the Chase Sapphire Reserve® (3x) or Chase Sapphire Preferred® Card (5x when booked through Chase Ultimate Rewars,2x on all other).

Related: Going on road trips this summer? Consider using these credit cards

And be sure to keep a great card for earning points on gas purchases in your wallet, too — especially if you're driving three hours or more outside Boston. With the Citi Premier® Card, you'll earn 3x points per dollar when you fill up at gas stations, along with 3x points on air travel, hotels, restaurants, and supermarkets and 1 point per dollar on everything else — ideal for a long weekend exploring New England, staying in charming inns and eating as much clam chowder as you can stomach.

If you're planning a near-term road trip, just remember that many states may still require out-of-state travelers to self-quarantine for two weeks. Maine's executive order , for example, requires a 14-day self-quarantine for visitors through much of the summer. Plus, many inns, restaurants and attractions may remain closed, at least to out-of-towners. So, you might want to bookmark these itineraries for later.

Related: 10 tips for anyone taking a road trip right now

Camden, Maine

Distance from Boston: 3 hours and 20 minutes

Often overshadowed by nearby Bar Harbor , Camden is a haven for outdoorsy travelers. Sure, visitors can spend an afternoon wandering up and down Main Street, stopping to admire the views of Camden Harbor or peruse the boutique shops (be prepared to spend too much on unexpected finds at Josephine on Elm Street). But to make the drive — just over three hours — worthwhile, travelers should take advantage of the destination's ample outdoor activities.

What to do : Explore Camden Hills State Park on the 30-mile trail network. One of our favorites is the moderate trail up to Ocean Lookout for an uninterrupted view of the town and harbor. If you're interested in something more, well, vertical, have Equinox Guiding Service bring you out for an afternoon of rock climbing. For a more relaxed option, head out to Savage Oakes Vineyard and Winery to sample their house blends, made with 10 grape varieties grown on-site.

Where to stay : Camden has a mix of lodging options, mostly small bed and breakfasts and inns. But 16 Bay View is Camden's newest luxury hotel, housed in a 100-year-old industrial brick building that once operated as a car dealership. For a more intimate stay, book a room at the Camden Harbour Inn , with rooms and suites that boast (as its name implies) exceptional views of the water.

What to eat and drink: Located in the Camden Harbour Inn, travelers should reserve a table on the porch of Natalie's Restaurant . If oysters are what you're after, head over to 18 Central Oyster Bar and Grill , in nearby Rockport, for a platter of their local or "away" raw oysters.

Related: Why you should visit Acadia National Park in Maine

Freeport, Maine

Distance from Boston : 2 hours

While Freeport is best known as the birthplace of LL Bean, there are plenty of other reasons to spend a weekend in town. Located just north of Portland on the shores of Casco Bay, brick buildings line Freeport's streets, and shoppers wander unhurried between the outlet stores and seafood-centric restaurants.

What to do : Start your trip to Freeport by stocking up on activewear and outdoor gear at LL Bean's flagship location, which is typically open 24 hours every day. Shoppers should also check the outlets at the Freeport Village Station. Just be sure to keep a great card for everyday spending , such as The Blue Business® Plus Credit Card from American Express or the Chase Freedom Unlimited, in the front of your wallet. Afterward, head over to DeLorme, in nearby Yarmouth, to see the world's largest rotating globe (it's nearly 42 feet across), or take a walk through the hemlock and white pine forests of Wolfe's Neck Woods State Park .

Where to stay : The Brewster House Bed and Breakfast is an upscale inn just three blocks from the center of Freeport. Seven rooms and suites make this a great choice for a romantic getaway, or for families exploring coastal Maine. Another option is the Harbour Towne Inn on the Waterfront — a Victorian-style bed and breakfast with panoramic views of Boothbay Harbor.

What to eat and drink : Start the morning with a cup of the daily roast from Coffee By Design , a sustainable cafe located inside the LL Bean store. Linda Beans is a favorite for seafood (order the classic Maine lobster roll) right on the main strip. Outdoor seating with fire pits makes this a great spot during cool, early summer evenings. Visitors should also sample Maine Distilling 's Blueshine blueberry liquor when the distillery is open for tastings.

Related: The 7 best 'secret' swimming holes to visit this summer

Stockbridge, Massachusetts

Surrounded by the mountainous terrain of the Berkshires , Stockbridge is a small town in rural Massachusetts with the culture and arts scene of a big city — with none of the traffic or crowds. Summers are usually filled with music festivals and theater, and travelers can also explore the area's extensive hiking and biking trails.

What to do: Founded in 1934, the Berkshire Botanical Garden (closed until further notice) is a 15-acre public garden that showcases local flora alongside contemporary sculpture exhibitions. Need a more strenuous activity? The Laurel Hill Association maintains three hiking trails in the Stockbridge area — the Mary Flynn Trail, Laura's Tower Trail and Ice Glen Trail. After a day of hiking or strolling through the gardens, travelers can typically catch an opera or theatrical performance at the historic Mahaiwe Performing Arts Center (closed until further notice). And, if you have the time to dedicate during your weekend trip, head to the Kripalu Center for Yoga and Health (closed for the remainder of 2020), a retreat offering a mix of yoga, writing and Ayurveda courses, among others. Programs typically last for at least two days.

Where to stay: The Stockbridge Country Inn is located within walking distance of multiple area museums. Its location on four acres of manicured lawns and gardens, complete with a patio and heated outdoor pool, make it a great place to relax and enjoy a hot summer afternoon. The Inn at Stockbridge is another option, with 15 rooms spread throughout a renovated barn, a Victorian-style mansion in which many original antiques remain and a cottage house. When Miraval finally welcomes visitors to its third resort in the Berkshires , guests can focus on wellness and mindfulness. After all, it wouldn't be a Miraval resort without a full spa experience. Miraval resorts occupy their own lane in the World of Hyatt award chart, and a free night will cost you 45,000 points, plus an additional 20,000 per night for an additional guest in your room.

What to eat and drink: Providing food and accommodations to visitors for over two centuries, The Red Lion Inn serves traditional New England cuisine (along with an expansive wine list featuring over 400 different selections). For classic European dishes (think: escargot pot pie), try Once Upon a Table , which also dishes up more hearty, regional fare (crab cakes, for example).

Related: 4 incredible fall foliage drives in the Northeast

Woodstock, Vermont

Distance from Boston : 2.5 hours

Located in the heart of the Green Mountains, Woodstock is the quintessential New England town. New openings and upgrades over the past few years have transformed this drive-by town into a popular (and rather upscale) getaway for New Englanders. A pedestrian-friendly downtown is filled with small shops, inns and restaurants, while the surrounding rural landscape invites visitors to explore and unwind.

What to do : As the Northeast's premier skiing destination during the winter months, many of Vermont's ski resorts are overlooked as soon as the snow melts. For this reason, the local ski hill, Suicide Six, has a new mountain bike park, which has miles of machine-built trails that are free to use. If extreme sports are not for you, take a tour of the Billings Farm & Museum when it reopens (you'll get a firsthand look at what farm-to-table actually means). Woodstock and the surrounding hills are also great for cross-country cycling. Travelers will discover rural roads that meander along streams and past historic farmhouses. Before driving back to Boston, drop by the farmer's market to stock up on fresh snacks.

Related: Attractions worthy of a family road trip in Vermont

Where to stay: The Woodstock Inn and Resort has 142 traditional rooms and suites that mix history (like handmade furniture) with modern amenities (think: Wi-Fi, Nespresso machines and flat-screen televisions). Located about nine miles from Woodstock in Barnard, Twin Farms is an exclusive five-star resort spread across 300 acres. The all-inclusive has a renowned culinary program — and a price tag to match.

What to eat and drink: With thousands of farms in the state of Vermont, food in the Green Mountain state is incredibly fresh. Worthy Kitchen , for example, has a rotating menu based on what's in season, as well as a beer list that showcases some of the state's finest craft breweries, including Hill Farmstead and the Alchemist. At Soulfully Good Cafe , visitors can try the signature cream apricot scones for a sweet breakfast on-the-go.

Related: Use your points and book a staycation at one of these 7 kid-friendly resorts

Narragansett, Rhode Island

Distance from Boston: 1.5 hours

This coastal Rhode Island town is a classic New England beach destination, with four of the state's arguably most popular beaches nearby. Visitors will get their fill of local seafood while exploring the oceanfront, or venturing to nearby Block Island or Newport .

What to do : Situated on 60 acres of state parkland, The Scarborough State Beach boasts more than 2,000 feet of sandy ocean frontage and is home to a newly renovated pavilion. Narragansett Beach may be one of the best on the East Coast, and if lighthouses and history are your thing, visit the historic Port Judith Lighthouse, which was first constructed in 1806. The Towers, or Twin Towers, is another landmark structure, and it's the only remnant of the Narragansett Pier Casino, which was the heart of Narragansett during the late 19th century. Today, the restored Towers typically host an assortment of events, including dance lessons and musical performances.

Related: 5 ways to explore Newport this summer

Where to stay : Many of the rooms at the Aqua Blue Hotel have full or partial ocean views (and balconies), and it's centrally located in town. There are also several bed and breakfasts, such as the Ocean Rose Inn , which overlooks Newport Harbor, Narragansett Bay and Jamestown Island. Eighteen new rooms were revealed in 2017 as part of a property renovation.

What to eat and drink : Built in the late 1800s by the U.S. Coast Guard, this granite structure is now home to the Coast Guard House , a seafood restaurant perched on Narragansett Bay. If you overslept, head to Crazy Burger (hear us out). In addition to an eclectic vegetarian-friendly menu with items like the Poco Loco Vegan Burger, the restaurant usually serves breakfast until 4 p.m. daily.

Additional reporting by Melanie Lieberman.

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20 best weekend getaways from Boston

Escape the city this spring by heading to these mountains, islands and towns all within a few hours of Boston.

While there are plenty of activities to enjoy in the city, sometimes you just want to hit the road and escape to the fresh air, country roads, and charming small towns. Use our guide for top spring getaways to plan your next trip. But if you can't take a whole weekend away, check out one of these day trips from Boston . And on ce you ’re back in town, get back into the swing of things by hitting up the  best museums , listening to some   stellar live music  and dining out at the   hippest restaurants in Boston .

RECOMMENDED: Full guide to the  best   things to do   in Boston . 

An email you’ll actually love

Best weekend getaways

1.  Nantucket Island

Nantucket is the place to be once the sun is shining. 

Eat at : or, The Whale ( 38 Main St, 508-825-5897 ) located right on the cobblestoned main street in downtown Nantucket, if the weather is still nice you can enjoy eating on or The Whale’s back patio.

Stay at: Hotel Pippa ( 5 Chestnut St, 508-228-5300 ) at the contemporary boutique hotel, guests can enjoy complimentary breakfast before setting out for the day. The team at Hotel Pippa is happy to assist guest booking a variety of island activities from fishing expeditions to cooking classes. When the day is done, guests can unwind on Hotel Pippa’s cozy patio. 

Must do: Visit in early October and travelers can enjoy a brand-new fall festival, The Harvest Fair ( 220 Milestone Rd ) which will take place October 1-2. Historically the Island Fair and the Cranberry Festival happened on separate weekends but 2022 will be the first year the events merge for one large festival.

2.  Newport, RI

Step back in time with a weekend getaway to Newport, RI. Home to the famed Newport Mansions, Newport is also packed full of waterfront dining, shopping, and plenty of options for getting outside and staying active.

Eat at: The Mooring Seafood Kitchen & Bar (1 Sayers Wharf 401-846-2260) pro-tip is to reserve a table around sunset on their deck overlooking the wharf. 

Stay at: For a romantic getaway in Newport check in at Castle Hill Inn ( 590 Ocean Ave 888-466-1355), the views cannot be beat. 

Must do: Touring the Newport Mansions  is a must, we recommend doing at least three. But save The Breakers for last as it is the most impressive! Afterwards, stroll along the Cliff Walk for world class views. Last, no trip to Newport is complete without a sail around the harbor, book an afternoon sail or an evening cocktail sail on the Adirondack II .

3.  Woodstock, VT

One of the most charming towns in all of New England. Woodstock is the perfect fall escape, travelers can visit local farms, museums, stroll through the town square and pop in and out of all the local shops.

Eat at : Worthy Kitchen ( 442 Woodstock Rd, 802-457-7281 ) definitely worthy of a visit. At Worthy Kitchen guests will find farm-to-table comfort food and local craft beers on tap.

Stay at: The Woodstock Inn & Resort ( 14 The Green, 888-338-2745 ) located right on the town square The Woodstock Inn is the perfect place to stay if you want to be centrally located to everything in town. Walking distance to tons of shops and restaurants, the Inn also has a world-class, LEED-certified Spa.

Must do: Sugarbush Farm ( 591 Sugarbush Farm Rd, 802-457-1757 ) offers free cheese and maple syrup tastings. You can explore the farm grounds, take in beautiful foliage views and do a little shopping in their farm store. If you’re visiting Woodstock in the fall, you have to take a ride out to Sleepy Hollow Farm ( 3429 Cloudland Rd South, Woodstock, VT 05091 ). A privately owned property, but you can view the charming farm from the road, you’ll likely be in good company with fellow photographers and leaf peepers.

4.  Provincetown, MA (PTown)

Leave the car at home because Provincetown is just a 90-minute ferry ride from Boston. With lots of fun bars, great restaurants, and plenty to do Ptown is one of our top weekend getaways from Boston for a reason.

Eat at : The Canteen (225 Commercial Street 508 487-3800) has beach front dining, an incredible lobster roll, and frosé. What more could you need?

Stay at: The Harbor Hotel Provincetown 's ( 698 Commercial St, 508-487-1711 ) retro-glam style and modern amenities makes it exactly what you want on a weekend away. Plus they’re pet friendly!

Must do : Enjoy off roading on a dune tour. Stop by Art’s Dune Tours for an exhilarating ride through the dunes, the team gives you a full history of the area, from how it joined the Cape Cod National Seashore to the history behind the artist shacks.

5.  Watch Hill, RI

Taylor Swift vacations in Watch Hill, why shouldn’t you? Just over two hours from Boston this small town is walkable and is home to the oldest continuously operating merry-go-round in the country.

Eat at : Olympia Tea Room (74 Bay Street 401-348-8211) is an institution. Just a short walk from the beach the simple menu has been keeping guests happy for over 100 years. 

Stay at : There are two clear winners when it comes to where to stay, the Ocean House ( 1 Bluff Avenue 855-678-0364) or the Watch Hill Inn (38-44 Bay Street 855-677-7686) . The Ocean House boasts its own private beach, multiple onsite dining options including Dalia , a new seasonal Coastal Mexican venue by Chef Dantón Valle, and croquet courts. The Watch Hill Inn is right on Bay St overlooking the harbor, and is convenient to all the shops.

Must do: Walk down to the Watch Hill Lighthouse , then spend the day shopping along Bay Street or head to the beach.

6.  Kennebunkport, ME

Just an hour and a half from Boston, Kennebunkport is the quaint seaside town you’ve been dreaming of. There is a little something for everyone in Kennebunkport (you may even spot the Bush family!). 

Eat at : Stop by Old Vines Wine Bar ( 173 Port Road (207) 967-2310) for outdoor seating and live music, their menu is filled with small snacks and sharables plates. However, the wine list and craft cocktails are the real draw. And no trip to Kennebunkport is complete without a stop at The Clam Shack ( 2 Western Ave 207.967.3321) , they’ve been serving fresh seafood since 1968!

Stay at : The Boathouse (21 Ocean Ave; 207-967-8225) brushes up against the Kennebunk River, which is easily viewed from your room’s oversized windows.

Must do : Visit Nubble Light . If you went to Kennebunkport for the weekend and didn’t take a picture of the famous lighthouse, did you really go?

7.  Mystic, CT

Home to Mystic Pizza and the Mystic Aquarium, this small coastal village, which is actually officially part of Stonington CT, is a great weekend getaway from Boston. 

Eat at: Mystic Pizza (56 West Main St. 860-536-3700) is worth a visit. But if you’re not in the pizza mood checkout Red 36 Bar & Grill (2 Washington Street 860-536-3604) for waterfront dining, fresh seafood and great cocktails.

Stay at: Stonecroft Country Inn Bed and Breakfast (515 Pumpkin Hill Road 860-744-5868)  is the quaint B&B that summer weekend getaway dreams sometimes require.  

Must do: Go brewery hopping . Mystic and Stonington are home to a handful of great local breweries including Barley Head Brewery, Bank & Bridge Brewing and Beer’d Brewing Co. Not into beer? There are also a bunch of great vineyards and wineries in the area.

8.  The Berkshires, MA

In need of fresh air? The Berkshires have you covered with museums, concerts, legendary authors' homes, hiking and more. 

Eat at : Methuselah Bar and Lounge (391 North St, Pittsfield; 413-347-2888) is focused on organic wines and craft beers, pairing them with funky, reimagined American fare, tacos and Korean-inspired dishes. Nudel: Comfort & Craft (37 Church St. 413-551-7183 ) post-pandemic this Berkshires favorite has been doing “pop-ups” that allows them to change their menu every few months to focus on fresh seasonal ingredients! 

Stay at : Seven Hills Inn (40 Plunkett St 413-637-0060 ) the former Gilded Age mansion offers 57 guest rooms, stunning gardens and an outdoor pool.

Must do : Be adventurous at Catamount Mountain Resort (Route 23 413-528-1262) go on a zipline tour, spend the day in the adventure park, or go on a scenic chairlift ride!

9.  Bar Harbor and Acadia National Park, ME

A little further afield, Bar Harbor is almost five hours from Boston by car so be sure to make the most of your weekend in Bar Harbor and add on a trip to Acadia National Park, the only national park in New England

Eat at: The Travelin Lobster (1569 ME-102 207-288-8028), have the lobster roll you won’t regret it.

Stay at: The Bar Harbor Grand Hotel (269 Main Street 207-288-5226) is a replica of the historic Rodick House, convenient to both downtown and Acadia. This hotel is the perfect spot to relax and unwind after a day of hiking.

Must do : Make the most of your weekend in Bar Harbor by doing a tour of Acadia National Park . Thsi is the most approachable way to see the park if you’re not a big hiker and want to see all the major landmarks in a short period of time. (The classic tour is only 2.5 hours leaving you plenty of time to explore on your own!)

10.  The White Mountain National Forest, NH

Even if you don’t know it, when you think of New England you are likely picturing the Kancamagus Highway. The scenic highway runs right through the heart of the White Mountain National Forest. The White Mountains are truly spectacular in the fall and winter, there are tons of charming small towns to stay in, great hiking and of course endless vistas.

Eat at: The Covered Bridge Farm Table Restaurant ( 57 Blair Rd, 603-238-9115 ) something about wood covered bridges just captures the essence of New England perfectly. The Covered Bridge Farm Table Restaurant is located at the bottom of the White Mountains and is the perfect spot to stop for lunch on your drive up or your drive back to Boston.

Stay at : The Omni Mountain Washington Resort ( 310 Mount Washington Hotel Rd, 603-278-1000 ) this historic New England hotel has views of the presidential mountain range, a world class spa and you can take a scenic gondola ride right across the street at Bretton Woods.

Must do: The Cog Railway ( 3168 Base Station Rd, 800-922-8825 ) want to take in the foliage from the summit of Mount Washington but not looking to take on the hike? The Cog Railway will take you on a dramatic climb up the mountain. The rail has been running for more the 150 years, be sure to book tickets ahead of time so you can take in the views on this must do experience.

11.  Martha's Vineyard

Martha's Vineyard is just a short ferry ride from Cape Cod that drops travelers right in either Edgartown, Oak Bluffs or Vineyard Haven for convenient access to shops, hotels and restaurants. Enjoy amazing beaches, see the Edgartown Lighthouse or take a ride to Island Alpacas for a truly one-of-a-kind experience.

Eat at: Visit Back Door Donuts (1-11 Kennebec Ave 508-693-3688) for the ultimate late-night snack, these donuts are worth waiting in line.  

Stay at : The Harbor View Hotel (131 N Water St 877-624-7992 ) cannot be beat. So many things including amazing views, sumptuous accommodations, complimentary bikes and the Mercedes-Benz Drive Program make it a luxurious home away from home. 

Must do: Whether using complimentary bikes provided by a hotel or renting bikes for the weekend, bikes are one of the best ways to explore the island. Martha’s Vineyard offers over 40 miles of trails and roadways through its scenic towns and along its coast.

12.  Block Island, RI

Located just 13 miles offshore, Block Island is a great alternative to Nantucket or Martha’s Vineyard, it is a bit quieter and more relaxed. Good news for our nature lovers, 40% of the island is conservation land, accessible only by bike or foot.

Eat at: Poor People’s Pub (33 Ocean Ave 401-466-8533) offers casual local seafood, burgers, pizza and more. They’re conveniently located by the Old Harbor Block Island Ferry and offer outdoor seating! Before heading back to the ferry, grab gourmet sandwiches from Three Sisters (443 Old Town Rd; 401-466-9661).

Stay at : Spring House (1401 Ocean Ave; 732-776-6700) , the island’s oldest hotel, entices with Adirondacks and a wraparound veranda overlooking the water. 

Must do: Go horseback riding on the beach. Visit Rustic Rides Horse Farm , the offer both beach rides and trail rides, a great way to see the island!

13.  Salem, MA

Want to get witchy? Salem attracts thousands of visitors every fall, people looking to embrace the spooky, supernatural, and witchy vibe of the small coastal town. It can get a little crazy in the two weeks leading up to Halloween, but a winter trip is just as fun! In addition to all the witch themed attractions there is also a buzzing art scene in Salem, great restaurants and travelers have to visit Far From the Tree Cider to do a tasting.

Eat at : Howling Wolf Taqueria ( 76 Lafayette St, 978-744-9653 ) keep things spooky with a red-hot ghost pepper infused margarita. Howling Wolf Taqueria is known for their massive burritos and their wolf bites like avocado fries and ceviche.

Stay at: The Merchant ( 148 Washington St, 978-745-8100 ) a Lark Hotel, The Merchant is conveniently located right down town. Walk to all the witch shops, great restaurants and plenty of nearby tours and museums.

Must do: If you want to embrace the spooky vibes in Salem sign up for a Candlelit Ghostly Walking Tour ( 288 Derby St, 978-740-2929 ). The hour long walking tour will take you around some of Salem’s most haunted locations. For travelers who want to see another side of Salem, plan a visit to the Peabody Essex Museum ( 161 Essex St, 978-745-9500 ) the world-renowned art museum has collections dating back to the 1700s including paintings, sculptures, photography and more.

14.  Portland, ME

Charming brownstones, bucket list worthy restaurants and ocean views? Portland is a great idea any time of year but especially in the summertime when you can take advantage of everything happening on the waterfront. Be prepared to eat all weekend long, Portland is a foodie’s paradise.

Eat at: You really can’t go wrong but three spots to get you started: Duckfat (43 Middle St; 207-774-8080 ) for fries, poutine and a milkshake when you're hungover the next day. Central Provisions (404 Fore St; 207-805-1085) for the locavore meal of the moment. And you must try Highroller Lobster Co (104 Exchange St. 207-536-1623) !

Stay at: Conveniently located in the Old Port, The Press Hotel (119 Exchange St; 800-971-2000) is the former home of the Portland Press-Herald and carries on the print tradition with newspapered walls, letterpress carpeting and leather desk chairs. Be sure to check out their amazing art collection.

Must do: Tour Casco Bay ! Experience Portland on the water as you visit all the islands throughout Casco Bay.

15.  Hartford, CT

Hartford is the perfect central location for several fantastic fall attractions tucked away in the heart of Connecticut. Stay in Hartford and plan a drive to East Hampton, home to Pumpkintown USA . Then book a fall foliage scene hot air balloon ride with CT Ballooning in Kensington.

Eat at : Max Downtown ( 185 Asylum St, 860-522-2530 ) a staple in Hartford for over 20 years this chophouse and whiskey bar is a must visit during your stay in Hartford. Dine in style and enjoy elevated classic in the recently renovated space.

Stay at: Delmar ( 1 Memorial Rd, 860-937-2500 ) this pet-friendly, luxury hotel is the perfect place to enjoy a weekend getaway to Hartford. The Delmar has a full-service spa, the fitness center features Peloton bikes and guests even get complimentary admission to the New Britain Museum of American Art.  

Must do: Use Hartford as your jumping off point to explore some of Connecticut’s best fall attractions like Pumpkintown USA ( 100 East High St, East Hampton CT ). If you want to spend a day exploring Hartford, plan a visit to Mark Twain’s House and Museum ( 351 Farmington Ave, 860-247-0998 ).

16.  Stowe, VT

New England is awash with winter resort towns, but we most love those areas that celebrate four-season recreation. Come summer, Stowe swaps out skiing for hiking, golfing, mountain biking and kayaking. Bonuses include swimming hole visits and scenic drives up the squiggly Auto Toll Road.

Eat at: Plate (91 Main St; 802-253-2691)  combines California cuisine with Vermont-sourced ingredients. Take the gondola up to Cliff House (5781 Mountain Rd; 802-253-3665) and enjoy a bottle of wine on the outside deck before hiking down afterward.

Stay at: Spruce Peak (7412 Mountain Rd; 802-253-3560 ) manages to feel homey and warm (also dog-friendly!), despite its luxury amenities. Added perk: It's also dog friendly, so your canine companions can come stay on vacay.

17.  Portsmouth, NH

Just a short ride from Boston, this seaside town has a rich history. While you may think it was the town’s role in the American Revolution or its history as a booming seaport that put it on the map, but Portsmouth is actually most well known as a hub for the brewing industry. There are 8 breweries travelers can visit right in Portsmouth!

Eat at : Botanica Restaurant and Gin Bar ( 110 Brewery Ln, 603-373-0979 ) this upscale French-influenced restaurant is the perfect spot for a romantic dinner, be sure to save room for dessert!

Stay at: Ale House Inn ( 121 Bow St, 603-431-7760 ) this boutique hotel is located right in the heart of downtown in what was once a warehouse for The Portsmouth Brewing Company.

Must do: Schedule your visit in October so you can partake in the annual Pumpkin Smash , taking place on Saturday October 28. All month-long travelers can check out the Scarecrows of the Port , unique scarecrow displays scattered throughout downtown.

18.  Providence, RI

One of the more underrated New England capitols, Providence also has an incredibly underrated food scene! This city is just a short ride on the commuter rail from Boston and is filled with New England charm and unique events like WaterFire .

Eat at : Hemenway’s ( 121 South Main St, 410-351-8570 ) is a top rated and local favorite. Hemenway’s offers an excellent raw bar and is the go-to restaurant for fresh seafood. If you’re looking for a great glass of wine, you’re in luck, in 2021 Hemenway’s received the Wine Spectator’s Award of Excellence.

Stay at : Graduate Providence (), formerly the Providence Biltmore this historic hotel recently got a complete renovation while maintaining some of the historic charm, like the lobby’s original ornate ceiling and glass-and-brass elevator. Located right downtown, guests are just a short walk to restaurants and shops.

Must do: Head to the Roger Williams Park Zoo (1000 Elmwood Ave, 401-785-3510) for the annual Jack-o-lantern Spectacular . Starting September 29 and running through October 31 visitors can take in thousands of artistically carved pumpkins. Throughout fall there will be 4 full lightings of WaterFire, a series of up to 100 bonfires floating on the three rivers of downtown Providence. See this award-winning installation on September 24, October 1, October 22, or November 5.

19.  Chatham, MA

The Cape is a no-brainer, but where to stake your claim? We’ve long migrated towards the inimitable charms of Chatham, where the homes will make you drool, the town center is walkable and crammed with cute boutiques, and the seafood is hauled in just offshore. 

Eat at: Impudent Oyster  ( 15 Chatham Bars Ave, 508-945-3545 ) offers innovative spins on classic seafood dishes and a lively bar inside a former church.

Stay at: Chatham Bars Inn (297 Shore Rd; 508-776-6700 ) is the ne plus ultra of Cape retreats for good reason: The cabana’d beach alone earns the resort its mythic reputation—and justifies the indulgence.

20.  Montreal, Canada

If you must flee the country, you might as well drive into the clutches of a cosmopolitan city bursting with history, nightlife, outdoor concerts and a shopping scene that invites closet do-overs.

Eat at: Martin Picard’s Au Pied de Cochon (536 Duluth Est; 514-281-1114) for foie gras on top of foie gras on top of poutine.

Stay at: Hotel Gault (449 St. Helene St; 514-904-1616 ) , a lavishly reappointed boutique hotel in Old Montreal. 

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The best road trips in America

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13+ Unforgettable Road Trips from Boston to Take This Year

Boston, a charming Northeast city, is best known for its role in American history. While there are plenty of things to do in Boston on its own , there are also so many surrounding cities and parks that are only a quick road trip from Boston that are also worth exploring!

Having grown up in California, I was not used to the accessibility of other states until living on the east coast! It’s as easy as hopping in your car, and you could be in another state or city near Boston exploring a state park, a beach, or a wine region!

With the help of my fellow travel bloggers, we have crafted a list of the best road trips from Boston that I encourage YOU to take this year!

So, let’s get into it!

Planning a trip in 2024? Check out some of my favorite resources!

For flights:.

Expedia makes booking flights extremely easy. I found that they always have the cheapest flights, and have not had any issues with their customer service.

For HOTELS:

I use Booking or all of my hotel reservations. The platform is extremely easy to use, and you always get the best rate because of their price guarantee.

For Activities:

I love booking activities before a trip with Get Your Guide! I have had a good experience with all of the activities I booked, and found they have the most affordable prices.

Disclaimer: This post may contain affiliate links. If you click on a link, we may earn a small commission if you purchase through these links at no additional cost to you.

Table of Contents

Map of the Road Trips from Boston Destinations

Here is a map showing all of the destinations that this list of the best road trips from Boston includes!

The Best Road Trips from Boston

On this list, you will find some road trips that will take you under an hour, and some that might even need to be broken up into multiple days! We’ve included the road trip length and distance to allow you to better plan your journey.

1. Boston to Mystic, CT

• Road trip destination: Mystic, CT
• Road trip length: 2 hours
• Road trip distance: ~100 miles
• Route taken: I-95 S
• Best time for road trip: June to August and during the fall foliage season (September/October)

Recommended by Kitty from  Kittymeetsworld

Driving to Mystic, Connecticut makes for an excellent road trip from Boston. The drive itself will take around two hours (and in fall offers a chance to admire autumn colors).

If you want to break up your journey, you could stop in Providence, RI, to check out the beautiful campus of Brown University and the downtown area. Closer to Mystic, Saltwater Farm Vineyard on the Connecticut Wine Trail would also make for a fun stop.

But, the highlight of this road trip is the destination . Mystic is the prototype of a traditional coastal New England town. With its clapboard houses, white church, tree-lined streets, and quaint stores, the historic downtown of Mystic is ideal for a stroll. If you time it right, you may even see the bridge being raised to let sailboats pass through!

Don’t miss out on a visit to Mystic Pizza, made famous by the 1988 film with Julia Roberts. If you would rather enjoy seafood in a casual atmosphere, nearby Noank has two popular lobster eateries. Watch out for seagulls though if sitting outside – they will steal your food if you are not careful!

Aside of the charming village that seems to be straight out of a Norman Rockwell painting, Mystic boasts another major attraction: Mystic Seaport. Seaport Village recreates life in a whale fishing village in the 1880s and is a must-see on your road trip.

In the summer and on weekends, docents in period clothing show traditional craft, fishing, and farming methods. In addition, you can explore historic boats and even take a ride on a steamboat.

2. Boston to the Berkshires, MA

• Road trip destination: The Berkshires, MA
• Road trip distance: 125 miles
• Route taken: I-90 W
• Best time for road trip: Summer

Recommended by Karen of Outdoor Adventure Sampler

The Berkshires in Western Massachusetts are an ideal road trip from Boston. Located a mere two hour drive from Boston, the vacation paradise of the Berkshire mountains is a spectacular place to explore. Take the Mass Turnpike for 125 miles to the western part of the state to access the many small towns.

Visitors are drawn to the outdoor beauty of the Berkshires in all seasons. Outstanding fall foliage is a showcase for travelers from all over the world. In the winter, the Berkshires become a snowy wonderland.  Cross country, snowshoeing, and downhill skiing areas  can be found throughout the Berkshires.

However, summer may be the most popular season to visit the Berkshires. Charming villages with boutique shops and farm to table restaurants abound. 

Besides outdoor activities, the Berkshires area is home to the Norman Rockwell Museum, the Clark Museum, and the innovative Massachusetts Museum of Contemporary Art (MassMOCA). The Berkshires also boasts the open air music venue Tanglewood. It has an immaculate lawn for spreading out a picnic while watching world-class concerts. The summer home of the Boston Symphony Orchestra is also at Tanglewood.

I enjoy spending a few days in the Berkshires to see some of the natural beauty such as Bash Bish Falls. It’s also easy to immerse in the culture and spend a few hours exploring the museums and historic towns. End the day with a stay in one of the classic New England inns with stone fireplaces and historic touches.

3. Boston to Chatham, MA

• Road trip destination: Chatham
• Road trip length: 1.5 hours with no traffic
• Road trip distance: 87 miles
• Route taken: take I-93 South out of Boston and then merge onto Route 3 South
• Best time to take road trip: Summer or Fall

Recommended by Fab 5 Family Travel

Chatham is one of the most beautiful destinations on the Cape, and recently was able to take this road trip with my husband on summer vacation! We flew into Boston and left directly from the airport. We arrived mid-morning, so didn’t experience much traffic but keep in mind the traffic worsens on Fridays and on the weekends as people flee the city for the Cape beaches.

We loved our stay at the Greyfinch Inn and our time exploring Chatham. Some of the best things we did were stroll through the charming downtown, see the seals at the Chatham Fish Pier, eat fresh seafood, and visit the iconic lighthouse.

Chatham’s beaches are gorgeous and a great way to unwind. If visiting in the summer, make sure to secure a parking pass for the popular beaches and catch a baseball game in the Cape Cod Summer League. 

While in Chatham, you must go to the Cape Cod National Seashore that stretches throughout the Cape. It was a highlight of our trip. If you love history, learn about the region’s history at Chatham Marconi Maritime Center or the Atwood House Chatham Historical Society.

4. Boston to Martha’s Vineyard, MA

• Road trip destination: Martha’s Vineyard
• Road trip length: 1.5 hours to Woods Hole then a 45 minute ferry ride to the island
• Road trip distance: 70-80 miles
• Route taken: I-93 South from Boston, merging onto MA-3 South, and then continuing onto US-44 West. Then I-495 South to MA-25 East. Follow signs to Cape Cod/The Islands.
• Best time to take road trip: Mid-week in early June for lighter crowds and pleasant weather. Avoid peak summer weekends if you’re not a fan of traffic. 

Recommended by Maria from Martha’s Vineyard Travel Tips

Martha’s Vineyard is the perfect destination for a road trip from Boston. If you time it just right, you can be sitting on the beach, basking in the sun less than 3 hours after leaving home. 

Some of my favorite things to do are to take a stroll around the colorful gingerbread cottages in Oak Bluffs or visit Edgartown Lighthouse. If you really want to get away from it all, I recommend hopping on the Chappy ferry and visiting the secluded, pristine beaches of  Chappaquiddick .

When you arrive on Martha’s Vineyard, you’ll find a charming island full of fascinating history, quaint shops, boutique inns and incredible local seafood restaurants. 

I’ve done this road trip several times and I recommend hitting the road early. Even though the journey is less than 80 miles, if you hit that Cape Cod traffic on a summer weekend, your driving time can double! It’s also essential to make a car reservation well in advance of your trip.

5. Boston to Salem, MA

• Road trip destination: Salem, Massachusetts
• Road trip length: 35 minutes
• Road trip distance: 25 miles
• Route taken: I-95, I-93, MA 128 N at Exit 40
• Best time to take road trip: Summer for great weather or Fall for Halloween festivities

Recommended by Mackenzie Jervis, A Wandering Scribbler

Heading out on a road trip through Massachusetts to Salem, MA, is not just a journey through miles but a voyage through time, history, and mystique. Salem, with its enigmatic past as the site of the infamous witch trials of 1692, has an intriguing blend of the eerie and the enchanting.

The road trip from Boston to Salem is only about 25 miles, offering a scenic drive through the charming New England landscape. Along the way, travelers can pause to explore historic landmarks such as Marblehead, known for its colonial architecture and maritime heritage.

In Salem, the cobblestone streets feel like stepping back in time. Attractions like the Salem Witch Museum and the House of the Seven Gables, where Nathaniel Hawthorne found inspiration for his novel of the same name, are great places to explore. While Salem is worth a visit any time of the year, the city truly comes alive in the fall. Salem’s Halloween festivities , held each October, are like a giant party throughout the town for those who love witches, spooky activities, and the history of the witch trials.

Salem also has a lively arts scene, with galleries, boutiques, and artisan shops lining its streets, offering a modern contrast to its historical significance. Salem’s food scene offers fresh seafood and locally sourced fare, while its waterfront promenade provides a serene backdrop for relaxation. Whether drawn by history, culture, or simply the allure of the unknown, a road trip to Salem from Boston promises an unforgettable adventure steeped in mystique and charm.

6. Boston to Ocean City, MD

• Road trip destination: Ocean  City, Maryland
• Road trip length: 7 hours
• Road trip distance: 450 miles
• Route taken: I-84 to CT-91 to CT-15 to Hutchinson River Pkwy to Cross County Pkwy to Henry Hudson Pkwy to I-95 to NJ Turnpike to 1-295 to 1-95 to US-13 to US-113 to US-50
• Best time to take road trip: Summer

Recommended by Denise from Chef Denise

A road trip to Maryland is a perfect way to spend a summer weekend! I’ve done this road trip from Boston to Ocean City many times, and it can easily be done in a day. However, I prefer to make some stops along the way as this route goes through two of America’s most amazing cities: New York City and Philadelphia. It’s even more worth it if you can spend a night in each. 

You can drive to Manhattan in about 4 hours from Boston. I like to leave early so I can have lunch in the city and take a long walk down 5th avenue and through central park. Then I have an amazing dinner, preferably where the view of the Brooklyn Bridge rivals the food.

From NYC to Philadelphia, it’s less than two hours. So I load up on a big breakfast at Veselka in the East Village before hitting the road. As a big foodie, in Philadelphia I’m happy wondering around Reading Market all day and landing where my taste bud take me. With a good dose of historical sights mixed in, of course. 

Then, it’s just 2.5 hours to Ocean City. Summer is the best time to visit Ocean City because as the name implies, this is a resort town that comes alive from Memorial Day through Labor Day. With a seven mile boardwalk, a warm Atlantic Ocean, and lots of water activities, the beach is where you’ll want to be. It’s also where you’ll find the  best crab restaurants in Ocean City —the real reason to visit in summer—crab season!

7. Boston to Acadia National Park, ME

• Road trip destination: Acadia National Park
• Road trip length: 5 – 7 hours
• Road trip distance: 300 miles
• Route taken: Highway 1 and 1A along the coast
• Best time to take road trip: Fall. The leaves and changing and the oysters are delicious

Recommended by Melody Fanslau from  The Winding Road Tripper  blog

A road trip to Acadia National Park is full of quaint towns and beaches, so it will be jam-packed with options for you to create your own trip depending on the amount of time you have.

One of the best parts about this road trip is it takes you along quiet highways along the coast (Highway 1 and 1A) and avoids Interstate 95.  

The best stops along this route include Salem, MA, Portsmouth, NH, Portland, ME, Camden, ME, and Bar Harbor/Acadia National Park, ME.

Salem hooked me with its eerie past and quirky museums. It was like walking through history with a spooky twist. Then, Portsmouth was a breath of fresh air—historic yet lively. Cafes, shops, and that old-world charm made it the perfect pit stop.

Maine was a showstopper with its scenic beaches and quaint towns. Portland was a blend of city cool and seaside charm. I had some of my favorite cocktails at Blyth & Burrows. The Portland Head Light was postcard-perfect, and wandering the Old Port was a day well spent.

Maine has many great coastal towns, but Camden was one of my favorites. You can spend time hiking in Camden Hills State Park or take a sunset sail. 

As for Acadia National Park, it was the grand finale. From the stunning views on Cadillac Mountain to the serene beauty of Jordan Pond, it was nature at its best.

This road trip was more than just a drive; it was a collection of awesome stops, breathtaking views, and delicious eats. Each stop had its unique flair, making the journey unforgettable.

8. Boston to Portsmouth, NH

• Road trip destination: Portsmouth, NH
• Road trip length: 1.5 to 2 hours with traffic
• Road trip distance: 62 miles
• Route taken: Interstate 95
• Best time to take road trip: September to November, during fall foliage season

Recommended by Stacy from Explore Baja California

Portsmouth is a historic city in that boasts a well-preserved downtown area with cobblestone streets, brick sidewalks, and elegant colonial architecture that is perfect for a weekend getaway from Boston.

If you don’t have a car, there are also bus services available between Boston and Portsmouth. Companies like Greyhound, C&J Bus Lines, and Concord Coach Lines operate several buses per day between these two cities. 

June to August is the peak season in Portsmouth. The weather is warm, and there are numerous outdoor activities and you can enjoy outdoor festivals, concerts, and dining. The downside is that it can get crowded, and accommodation prices may be higher during this time. 

September to November is fall foliage season in New England, including Portsmouth, which is renowned for its stunning colors. I visited Portsmouth in September and had a great time, as it was still sunny and pleasant to be around.  

The weather is generally pleasant throughout September and the first half of October, and there are still plenty of outdoor activities to enjoy, such as hiking and leaf-peeping. And, it is the visit fall-themed events and enjoy seasonal treats like apple cider and pumpkin-flavored treats at local farms and stores!

9. Boston to White Mountains, NH

• Road trip destination: White Mountains, New Hampshire
• Road trip length: Approximately 2.5 to 3 hours one way
• Road trip distance:  About 160 miles one way, depending on the specific destination within the White Mountains and the starting point in Boston.
• Route taken: I-93 North from Boston to the White Mountains. This route provides a direct path to many of the region’s attractions and scenic areas.
• Best time to take road trip: Fall

Recommended by Sophie from Delightful Travel Notes blog

A road trip from Boston to the White Mountains promises a mix of natural beauty, adventure, relaxation, and family fun. As you approach the White Mountains, the view transforms into a breathtaking vista with rugged mountain peaks, dense forests, and crystal-clear streams.

The best time to take this road trip is in the fall. Fall is a highly popular time to visit due to the spectacular fall foliage. The weather is also pleasant for hiking and outdoor activities.

Summer months are also perfect for those interested in hiking, camping, and other outdoor activities. The weather is warm, and all attractions and trails are open, including mountain coasters and water parks.

The area has a wide range of activities year-round but it is extremely beautiful in the fall. The forests become a vivid palette of reds, oranges, yellows, and golds. When visiting this region, we like to stay in North Conway, which is very convenient to access attractions and scenic drives, especially the famous Kancamagus Highway.

Due to its popularity, it is important to plan ahead if you want to see fall colors in the White Mountains. Accommodations can fill up quickly, and some areas may experience heavy traffic, especially on weekends.

10. Boston to Montauk, NY

• Road trip destination: Montauk, NY
• Road trip length: Around 5 hours
• Road trip distance: 202 miles
• Route taken: I-90 West, I-395 South, RT-32, then take Cross Sound Ferry
• Best time to take a road trip: Late spring is the best time to visit as you will get to experience warm temperatures but fewer crowds. 

Recommended by Samantha Oppenheimer of Find Love and Travel

I couldn’t recommend a better road trip from Boston than a trip to Montauk. You will find this wonderful beach town located at the end of the peninsula of Long Island, New York. Montauk is the perfect location for a spring or summer getaway! 

This is unlike any other locations that you’re probably familiar with in New York as it has a much more serene atmosphere, instead of the bustling streets and city lights. Plus, during your drive from Boston, you’ll get to experience some pretty incredible scenery, too.

The road trip is worth taking because there are so many great attractions to visit while there. Hiking and biking are both some of the best things to do in Long Island, and are very popular since there are six state parks to choose from. The Montauk Lighthouse is a great family-friendly activity. Then, after a day of driving and exploring, you can settle down on one of the beaches to enjoy an incredible sunset. Gin Beach is my favorite! 

11. Boston to New York City, NY

• Road trip destination: New York City
• Road trip length: Approximately 4 hours (with no stops)
• Road trip distance: 220 miles
• Route taken: There are multiple routes via I-90, I-95, or I-84 (each route offers different options for stops along the way)
• Best time to take the road trip: Summer or fall would be ideal

Recommended by Rebecca from Veggies Abroad

A road trip from Boston to NYC offers a scenic journey through picturesque small towns, ending with the Big Apple! If this is your first East Coast road trip adventure, I suggest taking the route via I-95 so you can enjoy a mix of scenery.

This route is especially great in the summer as you will have beautiful weather and longer days, but it’s also beautiful in the fall with the colorful foliage. I would avoid it in the winter, as the East Coast can be pummeled with snow and brutal winter weather. 

As you head to NYC via I-95, consider making two stops, first in Providence, Rhode Island, and second in the quaint town of Mystic, Connecticut.

In Providence, try to plan your trip around one of their unique WaterFire events! Generally, from late spring through fall, the city lights bonfires along the river, and there are activities and live music.

Mystic, Connecticut, is a charming small town known for its maritime museums, but it’s also the setting for one of Julia Roberts’s early movies, Mystic Pizza! The pizzeria that inspired the movie is still in town and serving up slices!

Once you get to NYC, you’re going to want to ditch the car — heads up, parking fees are astronomical! Just about every hotel offers parking, but be sure to check the prices before you book. NYC is one of the best cities in the US to explore. It’s home to endless entertainment, activities, and just about every type of food you can imagine, from greasy pizza to  fancy plant-based eateries.

12. Boston to Newport, RI

• Road trip destination: Newport, Rhode Island
• Road trip length: 3 hours
• Road trip distance: 156 miles
• Route taken: I-93 S to MA-24 S and RI-24 S to RI-114 S/W 
• Best time to take road trip: late Spring to early summer or late summer to early fall

Recommended by Jenifer of The Evolista

One of the best road trips from Boston is to the mansions of Newport, Rhode Island. The journey is only a few hours, and a step back in time to the Gilded Age. 

The Breakers, built as the summer residence for Cornelius Vanderbilt II, is the most notable of the Newport mansions. Step into 19th-century opulence and see the architectural grandeur of the Breakers. Then take the Cliff Walk, a scenic path with views of the Atlantic Ocean, to see Rosecliff, where many TV shows and movies have been filmed, and the Chinese Tea House at Marble House.

Fort Adams State Park is the largest fortification on the East Coast with cool tunnels and panoramic vistas of Newport Harbor. If you’re lucky, you may be able to see a concert or sailing race while there. 

Check out the shops on historic Thames Street and walk to Bannister’s Wharf for a meal at Clarke Cooke House Restaurant. On one of your days, take a sailing cruise or a ferry for a  day trip to Block Island . Once you arrive, rent a bike to tour Block Island’s beaches, lighthouses, and the Great Salt Pond. Have lunch at the Oar and order a mudslide before heading back to Newport. 

On the return trip to Boston, stop in Providence to visit the RISD Design Museum, Roger Williams Park and College Hill. This road trip is best done in 3-4 days and lets you experience a variety of New England bucket list activities.

13. Boston to Providence, RI

• Road trip destination: Providence, RI
• Road trip length: 1 hour
• Road trip distance: 51 miles
• Route taken: via I-93 S and I-95 S
• Best time to take road trip: October

Recommended by Tanya Taylor,  Travels & Treasures

Whenever I take a trip out of town I try to make the most of it and visit another city that is nearby.  So when I booked a girl’s trip to Boston, Massachusetts I thought it would be great to see Providence, Rhode Island. 

I booked a stay for two nights.  On the way, we enjoyed seeing the change of the colorful leaves during the Fall season.

The town was easy to get to and we only had to be on the road for 1 hour.  We settled into our hotel for the evening and awoke refreshed and ready to explore.

First, we went to Brown University and walked around the campus.  It was particularly interesting to learn that it was one of nine colonial colleges founded before the American Revolution. The downtown area was rather small but quaint.  The area is artsy with lots of boutique stores and unique finds.

My favorite experience was exploring Waterplace Park and Federal Hill.   Waterplace Park is situated along the Woonasquatucket River with pedestrian paths along the riverwalk.  It’s a great spot for a morning stroll or to grab bites and shop when the outdoor market is open.

Federal Hill is a happening neighborhood where locals hang out as a community.  We stopped at Costantino’s Venda Bar & Ristorante, an old Italian restaurant, and sat outdoors near a fountain while listening to live entertainment.  We were also fortunate to catch the start of the Rhode Island Seafood Festival in India Point Park. The stay was short, but the road trip inspired me to have more adventures.

14. Boston to Burlington, VT

• Road trip destination: Burlington, Vermont
• Road trip length: 5 hours and 40 minutes
• Road trip distance: 276 miles
• Route taken: MA-2, VT-9 W, Vt Route 7, I-91 (briefly)
• Best time to take road trip: May-July, September-October

Recommended by Amy Hartle of New England With Love

Vermont is a destination that calls to so many. Green as can be in the summer and vibrant with foliage in the fall, it’s my personal favorite state in New England. If you’re visiting Boston, it’s not a hop skip and a jump up to Vermont, but heading up and taking a  road trip through Vermont  is 100% worth it.

This trip can be done in one day if you’re feeling up to it, but I recommend a slower pace. If you take Route 2 straight out of Boston, you’ll pass Lexington and Concord: a must stop for history and literary buffs. Once you’re in Vermont, consider stopping overnight in Brattleboro, a fun hip town that’s a bit off the radar. 

After departing Brattleboro, you’ll cross over the mountains along Route 9, a winding road that is especially beautiful in the autumn. Don’t miss the scenic overlook in Marlboro at Hogback Mountain, which offers a “100-mile view.” Gorgeous. 

If Brattleboro doesn’t appeal, Bennington also has a lot of cool things to do, from art to coffee culture to its iconic Bennington Battle Monument. Leaving Bennington, you’ll drive up Route 7. You’ll follow this all the way to Burlington, with numerous possible sites to check out along the way. 

A couple of my favorites:

• Northshire Bookstore in Manchester: one of New England’s top independent bookstores
• Vermont Cookie Love in Ferrisburgh: incredible cookies, right along your route

Finally, you’ll be in Burlington. This is Vermont’s largest city and there is so much to do, including checking out the dozens of local breweries. Don’t miss views over stunning Lake Champlain either, especially at sunset. 

So now you know what the best road trips from Boston are! These road trips not only have an incredible destination to explore, but also include a beautiful drive (if taken during the right season!)

And, if you are looking for more Northeast cities to explore even after reading this, I’ve got you covered! Philadelphia is one of the best cities in the Northeast, with so many free things to do making it an affordable trip!

While I always recommend exploring a city enough to get a feel for it, Philadelphia is compact enough that you can easily craft a 1 day itinerary to explore much of what the city has to offer!

in it for later

Jess is a medical student in the midwest, with a HUGE passion for travel and wine tasting. When she is not found at the hospital, you can find her playing with her mini Australian Shepherd or planning her next vacation! She created Travel + Tannins to help inspire and plan travel (wine related, or not!) for others.

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16 Fun Road Trips from Boston Only A Short Drive Away

One of the best things about taking a trip to Boston is that there’s so much to do and it’s all so easy for you to get to. You can even take a day trip to New York and head back for the evening without having to worry about losing too much time!

In fact, arguably, the biggest challenge with planning a trip from Boston is narrowing down potential destinations. Plus, there’s an international airport to consider and the option of taking a cruise from Boston to see some of the world from the sea.

Here are a few of the destinations just a short drive away from Boston that you’ll want to consider, whether you’re a Boston resident or looking to book your next road trip. Pack some snacks for the family and hit the road!

This post is part of our North American Destinations Series – you can also read more great road tripping with kids ideas here

Trips from boston: a short drive away, 1. plymouth.

Plymouth, Massachusetts, shares its name with an old English seaside town, and it’s mostly known as the spot where the Mayflower docked and established a colony 400 years ago. There’s plenty of old architecture and historical monuments around Plymouth to see, and it also has a bunch of awesome museums and restaurants to visit.

Plymouth is particularly magical around Christmas, making it one of our favorite winter destinations in the US .

No, this isn’t a typo, and you’re not going crazy. Plimoth Plantation is a sort of living exhibit where you can walk around at your leisure and experience what life would have been like as one of the pilgrims who first settled there.

This is especially a great option if traveling with kids. Many of the original machines and technologies were around at the time, making it a great way to learn a little more about history and where we all came from.

Check out these incredible Airbnb properties around New England to complete your road trip!

3. Portsmouth

Okay, now we’re just playing with you. Don’t make the mistake of getting these three very different destinations confused with each other. This coastal city is also named after an English counterpart, and it’s a great spot for everything from boat trips and fresh seafood to museums and theatres.

Better still, it’s been growing and growing in recent years and now has the infrastructure to rival anything that any other city can throw at it.

4. Newport

Also named after a British place (this time in Wales), Newport is another stunning little coastal town with plenty to offer the casual visitor. In particular, we’d recommend strolling through Brick Market Place in the city’s downtown area, which is iconic for its delicious Chinese cuisine and the wide range of shops and stores that are on offer.

The Newport Mansion at Christmas is an unforgettable experience. And if you’re a car lover, you’ll want to stop by Portsmouth (also on this list) to visit the Newport Car Museum.

5. Newburyport

Seriously, what is it with these names? This coastal town has a lot in common with some of the others on this list, except that it’s a little less busy and so it’s easier for you to lose yourself in your own thoughts while wandering around the stunning scenery.

If you can get there in the summer, all the better – the street performers will be out in full force and the beaches will be just right for a bit of sunbathing. For a small town, there’s a lot to see and do in Newburyport .

6. Lincoln

Nestled at the base of the White Mountains in New Hampshire , there’s plenty to see and do in Lincoln throughout the year. In the winter, the town really comes alive, with a range of winter sports available as well as some of the most scenic ice skating rinks that we’ve ever come across. It’s a great place to take the kids if you’re looking for something magical in the run-up to Christmas.

7. Cambridge

Are you starting to see a theme here? Also named after our friends across the pond, Cambridge MA is just as intellectual as its British counterpart. As the home of Harvard, it’s also home to a bunch of different art galleries and museums that will satisfy even the most culture-obsessed travelers. And because even the smartest college students know how to party, there’s also plenty going on in the nighttime.

8. Providence

Located in Rhode Island, Providence is about an hour’s drive from Boston and makes for a great day trip if you want to see something a little bit different. It has regular festivals and celebrations throughout the year, so if you’re thinking about swinging by then it can be a good idea to spend some time looking at what’s coming up on the calendar; fall is a busy time with leaf-peeping road trippers in New England!

You’ll find plenty of fantastic places to eat, too. We recommend scoring some Italian food on Federal Hill.

9. Martha’s Vineyard & Nantucket

Martha’s Vineyard is one of only five US place names with apostrophes in the name, something which is technically against the law . In fact, it’s only been allowed to keep it because it has so much history, and that should give you a clue about why you might want to visit Martha’s Vineyard in the first place. And as you might expect from a place named after a vineyard, the food and drink scene is fantastic .

Nearby, Nantucket Island is known for its stunning beaches , picturesque lighthouses and crashing Atlantic waves.

10. Provincetown

Based on Massachusetts’ iconic Cape Cod , Provincetown is reminiscent of San Francisco in many ways because it’s a haven for artists, actors, musicians, and more, as well as a thriving LGBTQ+ community.

There are museums and art galleries almost everywhere you turn, as well as cool specialist stores and boutiques selling handmade goodies. There’s really nowhere else in Massachusetts that’s quite like it, and it’s sure to have something for everyone in the family.

11. New York City

As we mentioned earlier, New York City is just 4 hour’s drive away, and the city that never sleeps has so much going on that you could spend a month there and not run out of things to do.

Still, you can see quite a lot in a day trip or even spend the night there to give you a little more time – there’s plenty to see and do on the drive from Boston to New York City too; we’d strongly recommend extending your trip through Upstate New York .

You can read our family guide to exploring Manhattan here .

12. Castle Hill

You’d be crazy to skip a visit to this stunning 60-room mansion. You’ll feel as though you’ve stepped out of Massachusetts and into the middle of the English countryside. At only an hour’s drive away, it’s perfect for a half-day out. Pack a picnic and a blanket to enjoy lunch on the lawn.

13. Glendale Falls

Glendale Falls offers a great excursion by providing you with some of the most awe-inspiring natural beauty the state has. It’s one of the largest series of waterfalls in the country, and there are many trails to explore.

15. Concord

Concord is a relatively small town with a big history. It’s probably most well-known for being the site of a number of battlefields and as the haunting grounds of several key figures throughout history, including writers and statesmen. Walking through Concord, you know you’re retracing famous footsteps.

16. Lexington

Lexington is known for its battlefields too, including the iconic spot on Lexington Common where soldiers fired the first shot of the Revolutionary War. Many come in droves to learn more about the history of the area and the stunning country that we live in today. 

Want to extend your trip even further to Acadia National Park and the Maine coast? Try this road trip itinerary taking you all the way from Boston to Bar Habour on an epic new England Family road trip.

Planning your Boston day trips

Now that you know a few of the best places to visit while driving from Boston, it’s time for you to start planning your vacation. Remember, you can always combine multiple different destinations into a single trip by renting a car and going from city to city.

Because of that, it’s a good idea for you to go ahead and create a shortlist and an itinerary of your own, planning out where you’re going to visit, how long you’re going to stay, and which route you’re going to take.

By creating an itinerary and sticking to it, you can start to reserve hotels and other amenities to take advantage of early-bird pricing. This will save you money and also help you to avoid stressing too much in the run-up to your vacation. That way, you can just focus on having a fantastic time. Happy travels!

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Travel and Blossom

A travel and lifestyle blog for female solo travelers who want to learn how to travel with confidence

30 Best Road Trips From Boston

Fall Travel , North America , Spring Travel , Summer Travel , Winter Travel / April 2, 2022 by Jade / 16 Comments

Planning a road trip from Boston and don’t know where to go? Check out this post on the 30 best road trips from Boston.

As someone who doesn’t know how to drive yet, I’ve been dying to do a road trip out of Boston for quite some time now. However, until I’m able to get my license, my dream road trip out of Boston will have to wait. So, instead of pouting about as I wait for my license, I’d rather take this time to tell you some of the best road trips you can take out of Boston.

Table of Contents

New England Bucket List Series

P.s. this is a post in my new england bucket list series. here is the complete series:.

Road Trips: 30 Best Road Trips From Boston

Ice Skating: The Top 7 Places for Free Ice Skating in Boston

Hiking: 20 Best Hikes for Fall Foliage in New England

Fall Foliage: 12 Best Places for Fall Foliage in Boston

Thrift Stores: The 7 Best Thrift Stores in Boston for Vintage

Salem: One Day in Salem Massachusetts: Hocus Pocus Edition

Museums: The Top 8 Free Museums in Boston for College Students

Newport, RI (best road trips from Boston)

A trip to Newport, RI is one of the best road trips you can take out of Boston! The road trip will take about 90 minutes by car and there are a lot of fun things to do ! In fact, according to Pamela, Aquidneck Island is also home to Newport! In the island, you will find a lot of breathtaking sea cliffs around the Cliff Walk. The Cliff Walk is a 3.5 mile walk around the shore that shows off the breathtaking views of the mansions and the area. The Breakers is one of the most famous mansions around the area and it has tours available all year round .

Newport is also most popular during the summer due its wide range of water-based activities. Boats line the water all around Newport, and sailing is a common pastime in the area. However, if you’re visiting during the spring or fall, the nature’s colors will also inspire you!

The Naval War College Museum is also worth checking out if you’re looking to learn more about Newport’s history. Bowen’s Wharf and its neighbor Bannister’s Wharf , are even home to a variety of locally-owned shops and restaurants!

Overall, the elegant blend of history, nature and food is what makes Newport a great road trip to take from Boston.

By: Pamela of Directionally Challenged Traveler

Portland, ME (best road trips from Boston)

A trip to Portland, ME is another great road trip you can take out of Boston! The road trip will take about an hour and 45 minutes to complete and you can do a lot of fun things while you’re there .

In fact, according to Kelly, while the fastest way to get to Portland from Boston is via I-95, this highway can often become inundated with traffic once in a while. Therefore, if you have the time, taking Route 1 along the coast is your best option. Not only will it show you some sweeping views of the Atlantic, but you can also make some stops at some iconic places along the way like Ogunquit , Old Orchard Beach , Kennebunkport , and Cape Elizabeth .

In addition, feel free to make a pit stop at the Holy Donut on your road trip if you need food. You can order a sea salt and chocolate potato doughnut once you’re there as well as some coffee.

By: Kelly of Girl with the Passport

Newburyport, MA (best road trips from Boston)

A trip to Newburyport is another great road trip you can do from Boston! The road trip will take about 45 minutes to complete and you can stop by Salem on the way there too.

In fact, according to Newburyport.com , there’s no shortage of things to do in this city. For example, the Clipper City Rail Trail is a 1.1 mile path that runs from the MBTA all the way to the Merrimack River Shoreline. You can run, walk, or bike on this path as you pass by some popular spots like the Graf Ice Skating Rink or the Cashman Park .

In addition, the Waterfront Park is another popular spot you can go to in Newburyport. It has ample green space that is used for sunbathing, relaxing, and hosting events.

Portsmouth, NH (best road trips from Boston)

Portsmouth, NH is another great road trip you can take out of Boston. The road trip will take about an hour to complete and you can visit the Market Square once you’re there.

In fact, according to Planet Ware, there are a lot of top-rated attractions and things to do in Portsmouth. For example, Prescott Park is a popular attraction that is located along the banks of the Piscataqua River. It has beautiful gardens of perennial flowers as well as a performance space and public docks.

In addition, the Prescott Park Arts Festival is also held at the park. This festival brings in many theater performances each summer as well as music.

Provincetown, MA (best road trips from Boston)

A trip to Provincetown is another great road trip you can take out of Boston! The road trip will take about two hours and a half to complete and you can do a lot of fun things while you’re there.

In fact, according to Vicky, you can take a sand dune tour at Provincetown’s Cape Cod National Seashore Park as well as climb to the top of the Pilgrim Monument for some amazing views.

In addition, there are many different art galleries you can visit in town. The gallery district is located in Provincetown’s East End section and it has Friday night art openings every week .

By: Vicky of Buddy The Traveling Monkey

Westerly, RI (best road trips from Boston)

A trip to Westerly, RI is another great road trip you can take out of Boston! The road trip will take about two hours to complete and you can check out Taylor Swift’s house once you’re there.

In fact, according to Business Insider , Taylor Swift bought the Rhode Island mansion for 17.75 million in 2013. She even paid for the entire mansion in CASH ! Imagine that. Taylor Swift is not only wealthy but she’s also not afraid to make a grand gesture.

Since then, the musician is continuing to put her home to good use by hosting A-list parties and events.

Lake Champlain, VT (best road trips from Boston)

A trip to Lake Champlain is another great road trip you can take out of Boston. The road trip will take about five hours to complete and you can visit the Waterfront Park once you’re there.

In fact, according to Inspirock, Lake Champlain also offers a range of different activities for outdoorsy fans as well as an exciting food scene. For example, the Burlington Bike Path is a great path near Lake Champlain where people can ride their bikes along the lake.

Lake Champlain also has a shop called Lake Champlain Chocolates where people can buy chocolate bars, truffles and caramels.

Plymouth, MA (best road trips from Boston)

A trip to Plymouth, MA is another great road trip you can take from Boston! The road trip will take about 40 minutes to complete and you can visit Plymouth Rock once you’re there.

In fact, according to Planet Ware, there are a lot of top-rated attractions and things to do in Plymouth. For example, the National Monument to the Forefathers is a popular tourist attraction that is located along Allerton St in Plymouth. The monument commemorates the founders of the Plymouth colony and it was dedicated in 1889.

In addition, try to see if you can do a Native Plymouth Tour once you’re there. This tour will help you see all that Plymouth has to offer with a Native American perspective.

Rockport, MA (best road trips from Boston)

Rockport, MA is another great road trip you can take from Boston! The road trip will take about an hour to complete and you can snap pictures at Motif #1 once you’re there.

In fact, according to Addison Choate, Rockport has plenty of things to do that are under the radar. For example, just off the coast of Rockport you can visit Thatcher Island , an island known for its shipwrecks and for serving as a home for the mafia hitman turned informant, Joe Barboza .

He was a hitman for the Patriarca crime family during the 1960s and was a resident of the island back in 1967.

York, ME (best road trips from Boston)

A trip to York, ME is another great road trip you can take out of Boston! The road trip will take about an hour to complete and you can visit some other beautiful towns in Maine once you’re there.

In fact, according to Amanda, York has that classic coastal New England charm with its clapboard houses and stark white lighthouse. That stark white lighthouse in particular is called the Nubble Lighthouse .

Built in 1879, it is known to be haunted in York, ME by the ghost ship Isadore that wrecked nearby. If you’re interested in entering the lighthouse on your trip, go at your own risk. The lighthouse is not currently open to the public so it will be difficult.

By Amanda of Hey! East Coast USA

Block Island, RI (best road trips from Boston)

A trip to Block Island is another great road trip you can take out of Boston. The road trip will take about three hours to complete and you can go bike riding, kayaking and parasailing once you’re there.

In fact, according to New England With Love, there are a lot of other things you can do on the island as well. For example, you can check out the views at the Mohegan Bluffs .

The Mohegan Bluffs are large clay cliffs that are located on the south shore of the island. They have views that are undoubtedly the best on the island, as you take in the scenery from the water and the beach.

Acadia National Park, ME (best road trips from Boston)

A trip to Acadia National Park is another great road trip you can take out of Boston! The road trip will take about five hours to complete and you can visit the Park Loop Road once you’re there.

In fact, according to James Ian, when you get to Bar Harbor, the gateway town to Acadia National Park, you can easily spend another few days there or even a week.

The area is known for its prime lobster fishing hub in Maine where you can order fresh seafood right from the water’s edge.

In addition, Acadia National Park is a hiker’s paradise. It has dozens of trails available through the woods that offer incredible views of the surrounding oceans and islands. These trails include but are not limited to the Beehive and the Precipice .

By: James Ian of Parks Collecting 

Charleston, RI (best road trips from Boston)

Charleston, RI is another great road trip you can take out of Boston. The road trip will take about two hours to complete and you can visit the East Beach while you’re there.

In fact, according to Vacation Idea , there are a lot of other things you can do in Charleston as well. For example, Charleston has a top rated tourist attraction called the Fantastic Umbrella Factory .

It is known as a 19th century farmyard shoppers paradise in Charleston where visitors can shop at stores and admire local artwork. These stores include but are not limited to the General Store and the Frills. Local artwork can also be admired in the factory at the Henna Body Art.

Gilford, NH (best road trips from Boston)

Gilford, NH is another great road trip you can take from Boston! The road trip will take about an hour and a half to complete and you can visit the Gunstock Mountain Resort once you’re there.

In fact, according to Vacation Idea , there are a lot of other things you can do in Gilford as well. For example, Gilford has a top rated tourist attraction called the Pepi Herrmann Crystal Gallery and Museum that features a wide range of crystal objects’d art like jewelry, Christmas ornaments, barware, home decor pieces, and stemware.

So, if this is of interest to you, feel free to stop by this attraction on your trip. Once you’re there you can also purchase and take home a small, inexpensive gift.

The Berkshires, MA *in general* (best road trips from Boston)

In the winter, a trip to the Berkshires is another great road trip you can take out of Boston! The trip should take about two hours to complete and you can go cross country skiing and snowshoeing once you’re there.

In fact, according to Karen, numerous hikes are also available through the Berkshire Hills. These hikes include but are not limited to Race Brook Falls, October Mountain Loop and the Bash Bish Falls.

The Bash Bish Falls in particular is where you can go to admire the highest waterfall in the state.

By: Karen of Outdoor Adventure Sampler

Gloucester, MA (best road trips from Boston)

A trip to Gloucester, MA is another great road trip you can take out of Boston. The road trip will take about 50 minutes to complete and you can visit the Good Harbor Beach once you’re there.

In fact, according to Addison Choate, Gloucester has plenty of things to do that are completely under the radar. For example, in Gloucester, you can visit the Hammond Castle Museum that’s located in the Magnolia area on the Atlantic coast.

The castle, which was constructed between 1926 and 1929, was also the home and laboratory of John Hays Hammond, Jr ., who was an inventor and pioneer in the study of remote control.

Lexington, MA (best road trips from Boston)

A trip to Lexington, MA is another great road trip you can take out of Boston. The road trip will take about 30 mins to complete and you can visit the Wilson Farm once you’re there.

In fact, according to Trip Savvy , there are a lot of other things you can do in Lexington as well. For example, in Lexington, you can visit the Lexington Battle Green where the American Revolution began. This spot also showcases the Revolutionary Monument which dates all the way back to 1799.

In addition, the Lexington Venue is also a great place to catch a movie. It’s a small town movie theater with two screens that shows a variety of feature and independent films.

Plum Island, MA (best road trips from Boston)

A trip to Plum Island is another great road trip you can take out of Boston. The road trip will take about an hour to complete and you can visit Bob Lobster once you’re there.

In fact, according to New England, there are a lot of other things you can do in Plum Island as well. For example, on the island, you can visit Plum Island Beach which is 42 miles away from Downtown Boston.

Therefore, if you’re planning on checking out this spot for the first time, I highly recommend going before sunset. This will give you the chance to see the beach as the sun sets so that you can take great pictures.

Kennebunkport, ME (best road trips from Boston)

A trip to Kennebunkport, Maine is another great road trip you can take out of Boston. The road trip will take about two hours to complete and you can visit the Seashore Trolley Museum once you’re there.

In fact, according to Vacation Idea , there are a lot of other things you can do in Kennebunkport as well. For example, Kennebunkport has a top rated tourist attraction called the First Families Kennebunkport Museum.

It is operated by The Kennebunkport Historical Society and you can find it in an 1853 Greek Revival home on Main Street in a village.

Lenox, MA (best road trips from Boston)

A trip to Lenox, MA is another great road trip you can take out of Boston! The road trip will take about three hours to complete and you can visit The Mount, Edith Wharton’s Home once you’re there.

In fact, according to New England With Love, there are a lot of other things you can do in Lenox as well. For example, Lenox has a top rated tourist attraction called the Berkshire Scenic Railway Museum .

It is an all-volunteer, non-profit organization dedicated to preserving the history of railroading and trolley lines in the Berkshire Hills of Western Massachusetts.

Ipswich, MA (best road trips from Boston)

A trip to Ipswich, MA, is another great road trip you can take out of Boston. The road trip will take about 40 minutes to complete and you can visit the Castle Hill on the Crane Estate once you’re there.

In fact, according to Travel Lens, there are a lot of other things you can do in Ipswich as well. For example, in Ipswich, you can meet some wolves at a top rated tourist attraction called the Wolf Hollow .

It is a non-profit wolf sanctuary and educational hub that’s dedicated to preserving the wolves in the wild with education and exposure.

Ogunquit, ME (best road trips from Boston)

A trip to Ogunquit, ME is another great road trip you can take out of Boston! The road trip will take about an hour and 20 minutes to complete and you can visit Ogunquit Beach once you’re there.

In fact, according to Visit Maine, there are a lot of other things you can do in Ogunquit as well. For example, in Ogunquit, you can visit a top rated tourist attraction called Perkins Cove.

It is a small turn of the century fishing village that draws in great crowds every summer due to the boutique shops and fresh seafood.

Kittery, ME (best road trips from Boston)

A trip to Kittery, ME is another great road trip you can take out of Boston. The road trip will take about an hour to complete and you can visit the Kittery Historical and Naval Museum once you’re there.

In fact, according to The Crazy Tourist , there are a lot of other things you can do in Kittery as well. For example, in Kittery, you can visit a top rated tourist attraction called Badger’s Island.

Badger’s Island is an island that sits right in the middle of the Piscataqua River where several important boats were built many years ago. These boats include but are not limited to the Ranger, America, and Raleigh.

Westford, MA (best road trips from Boston)

A trip to Westford, MA is another great road trip you can take out of Boston. The road trip will take about 45 minutes to complete and you can visit The Butterfly Place once you’re there.

In fact, according to Boston Central , there are a lot of other things you can do in Westford as well. For example, in Westford, you can visit a top rated tourist attraction called Kimball Farm Mini Golf .

This attraction has two 18 hole adventure style miniature golf courses as well as a 6000 square foot bumper boat pond.

Fall River, MA (best road trips from Boston)

Fall River, MA is another great road trip you can do out of Boston! The road trip will take about an hour to complete and you can visit Battleship Cove once you’re there.

In fact, according to Kathyrn, this small city has many unique stops to offer to your average road tripper. For example, just down Water Street, you’ll find the City Gates Plaza, which is a tribute to the city’s sister city of Ponta Delgata.

In addition, this city also has the home of the famous axe murderer, Lizzie Borden . However, since the home is vacant, it is now being used as a Bed & Breakfast for tourists. So, if you like dark tourism and psychopathy, this spot is for you!

By: Kathryn of Staying Afloat Blog

Middlefield, MA (best road trips from Boston)

A trip to Middlefield, MA , is another great road trip you can take out of Boston! The road trip will take about three hours to complete and you can visit the Glendale Falls once you’re there.

In fact, according to Tripadvisor , there are a lot of other things you can do in Middlefield as well. For example, in Middlefield, you can check out Andrew’s gallery, DeVries Fine Art International Inc. , at the River Studio in the city.

The studio also has different series of Andrew’s sculptures that include but are not limited to dance, figurative, and abstract.

Sutton, MA (best road trips from Boston)

A trip to Sutton, MA is another great road trip you can do from Boston! The road trip will take about an hour to complete and you can hike the Purgatory Chasm once you’re there.

In fact, according to Sutton Mass, there are a lot of other things you can do in Sutton as well. For example, in Sutton, you can visit a top rated tourist attraction called Waters Farm .

In Waters Farm , you can enjoy horse drawn carriages in the summer, sleigh rides in the winter, and a wealth of other fun activities in between.

In fact, in my opinion, summer is the best time to visit since you’ll have the opportunity to participate in one of their festivals.

New Bedford, MA (best road trips from Boston)

A trip to New Bedford is another great road trip you can take from Boston! The road trip will take about an hour to complete and you can follow the Self-Guided New Bedford Art Walk once you’re there.

In fact, according to Kathyrn, this small city has many unique stops to offer to your average road tripper. For example, in New Bedford, you can explore a beautiful collection of murals scattered across the city.

In addition, you can also immerse yourself in New Bedford’s beautiful architecture by walking along the city’s cobblestone streets.

Cape Cod, MA *in general* (best road trips from Boston)

A trip to Cape Cod is another great road trip you can take out of Boston! The road trip will take about an hour to complete and you can stop by the Cape Cod National Seashore once you’re there.

In fact, according to the U.S. News and World Report , there are a lot of other things you can do in Cape Cod as well. For example, in Cape Cod, you can visit a top rated tourist attraction called Cape Cod Rail Trail.

Previously known as the Old Colony Railroad corridor, the Cape Cod Rail Trail is considered to be one of the best biking trails in New England.

Agawam, MA (best road trips from Boston)

A trip to Agawam, MA is another great road trip you can take out of Boston! The road trip will take about two hours to complete and you can visit Six Flags New England once you’re there.

In fact, according to Theme Parks and Entertainment , Six Flags New England is known for having some of the best roller coasters in the world. These roller coasters include but are not limited to The Great Chase, Catwoman’s Whip, and Goliath.

Superman The Ride is also the best ranked roller coaster in the park while The Great Chase is the worst.

Overall, I really hope you enjoyed this post on the 30 best road trips you can take from Boston! Please let me know in the comments down below which road trip destination you would like to visit the most! I would love to hear from you. 🙂 P.S. If you’re looking for some things to do in NYC, check out this post on the 101 things you can do alone while you’re there.

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Reader interactions.

April 7, 2022 at 16:36

Great road trips, I would love to be able to get across to take one or two soon…..

April 7, 2022 at 14:29

Acadia National Park would be my top weekend trip, hiking plus eating the best lobsters is hard to beat!

April 7, 2022 at 15:10

April 6, 2022 at 17:50

So many great ideas here, and such beautiful scenery. I would definitely look at basing myself in Boston and doing day trips

April 6, 2022 at 20:07

Thank you so much Elyse!

April 6, 2022 at 17:02

this native Bostonian approves of this list! Great recommendations and some of my favs spots (Gloucester, Newport)

April 6, 2022 at 17:04

Thank you Jennifer!!! 💓

April 6, 2022 at 16:37

OMG, I pretty much want to do ALL of these! I’m going to need a little time in Boston!

I KNOW RIGHT

April 6, 2022 at 16:28

This is such a great post with so many awesome recommendations! We traveled to Newport, Portland, Portsmouth, and Plymouth during our time in Boston this summer and are dying to go back to explore some more of these. Thanks for sharing!

April 6, 2022 at 16:31

You’re so welcome Brittany! I’m glad you enjoyed it.

April 4, 2022 at 14:07

So many fantastic places to go. How fun. Thanks for sharing.

April 4, 2022 at 17:46

You’re so welcome!

April 3, 2022 at 07:56

Oh so many beautiful places that you can visit from Boston! great inspiration for future!

April 3, 2022 at 10:01

Thanks Lasma!!

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30 Best Road Trips from Boston: Destinations To Explore

Boston is an incredible place, one that I lived in for several years. But every so often, I needed to get out of the city and make a day trip somewhere nearby. Boston is central to a number of places, and here are my suggestions for the best road trips from Boston. I sort them by distance, so you can choose the trips that best fit your schedule.

Where Can I Drive To From Boston?

If you have a vehicle, I would absolutely recommend leaving Boston, but if you’re going to stay in the city, read my article about Driving In Boston or Best Food in Boston . Within 6 hours of Boston, you can hit the Quebec Province of Canada , Maine , New Hampshire , Vermont , Connecticut, Rhode Island, New York, New Jersey, and Pennsylvania.

Is driving in Boston hard? Find out here !

What cities are within driving distance from Boston?

We defined driving distance as within 6 hours. That gives you time to make the drive there, explore and make it back in less than a day. So, here is our list of 30 best road trips within driving distance of Boston.

Where can you drive in 6 hours from Boston?

Lancaster, pennsylvania (6 hours: 2 minutes).

In a world in which malls are becoming less common, Park City Center Mall is the largest mall in South Central Pennsylvania with over 150 stores. Also in town is the Lancaster Central Market, the oldest continuously operated farmers market in the US. Which sells Amish goods not commonly found anywhere else. Finally, for watch enthusiasts, the National Watch & Clock Museum has the largest collection of closes and watches in North America.

Quebec City, Quebec (5 Hours: 58 Minutes)

Located on the north bank of the St Lawrence River, this Canadian city has lots of European designs to it. Areas such as Vieux-Quebec, Chateau Frontenac, and Notre-Dame de Quebec Cathedral have beautiful architecture. Just note that the primary language is French, you’ll still find some English speakers in the more touristy areas.

Atlantic City, New Jersey (5 Hours: 26 Minutes)

Known for its casinos, boardwalks and beaches, this is a popular tourist destination. Additionally the 9 casinos in one city is one of the ways it resembles a smaller version of Las Vegas. They also have 3 large shopping centers, 2 convention centers, and numerous beaches. Lastly, for fans of Monopoly, all of the spaces are named after locations in and around Atlantic City.

Philadelphia, Pennsylvania (5 Hours: 2 Minutes)

The largest city in Pennsylvania, and one of the leading cities in higher education in our country with 18 universities and colleges. Philadelphia was also our first US Capital which means there is lots of history in it. Additionally, the most famous monument being the Liberty Bell. is found here. The city has the most outdoor sculptures and murals of any US city.

Syracuse, New York (4 Hours: 31 Minutes)

Incorporated in 1825, Syracuse has grown substantially as a major hub and education center of New York with Syracuse University and two SUNY universities. With a huge arts focus, it is home of the Syracuse Jazz Festival and Polish Festival. It also has orchestras, opera companies, several theatres, and 5 museums.

Bar Harbor, Maine (4 Hours: 27 Minutes)

Located on Mount Desert Island and is home to Acadia National Park. Acadia National Park is a beautiful coastal park with hiking trails, boating, and camping. Home of Jackson Laboratory and MDI Biological Laboratories with a focus on marine life research. With over 2 dozen hotels and nearly 200 cruises arriving every year, it’s evident that this is a tourists favorite destination.

Long Island, New York (4 Hours: 12 Minutes)

The longest and largest island in the contiguous United States, Long Island is the most populated island anywhere in the US. With 8 big sports stadiums, golf courses, horse racing, and the national tennis center. It is truly a great place for sports lovers. In addition to theatres, music venues, and other entertainment venues, it’s definitely got the big city feel.

Road Trip Destinations around 3 hours from Boston

New york city, new york (3 hours: 12 minutes).

What’s better than a road trip to the Big Apple? With 5 boroughs, hundreds of diverse neighborhoods, skyscrapers, and Broadway, you could spend weeks in New York without getting bored. It is the city that never sleeps for a reason. Just note, that traffic in and near New York City can be a nightmare.

Pro Tip : if the traffic and parking in NYC is stressful, consider taking a train! It takes about as long as driving but you don’t have to worry about a car.

Danbury, Connecticut (3 Hours)

Nicknamed the “Hat City” due to its ties to the hat industry. Danbury is ranked as the most diverse city in New England by WalletHub. With lots of parks, hiking trails, and a railroad museum, there are some fun things to see and do. If you like old buildings, they have 12 on the National Registry of Historic Places.

Schenectady, New York (2 Hour: 59 Minutes)

Settled in 1661, this small (10.98 square mile) city still has lots to offer. With a golf course ranked as “Best places to play” by Golf Digest. This small city also boasts some beautiful architecture, as well as the first planned residential neighborhood and college campus. The Rivers Casino and Resort is worth visiting as well.

Bridgeport, Connecticut (2 Hours: 54 Minutes)

The largest city in Connecticut, and a major shipping port, this city got its start in 1821. Infamous showman P.T. Barnum was a resident and housed his circus in Bridgeport in the winters. Home of the world’s first Subway restaurant and where the electric plug outlet was invented. Additionally with 1,300 acres of green space in 35 community parks, the city has earned the nickname “Park City.”

North Conway, New Hampshire (2 Hours: 52 Minutes)

A small little town in New Hampshire, North Conway was originally chartered in 1765, nestled in the White Mountains. A perfect place for those who love outdoor activities. The Echo Lake State Park provides boating, swimming, and rock climbing. In the winter, Cranmore Mountian Resort provides 200 acres and 54 trails of skiing.

Trumbull, Connecticut (2 Hours: 52 Minutes)

With 20 local parks and one big state park, Trumbull has lots of green space to enjoy. In addition to the parks, they have four sites on the National Registry of Historical Places. If you happen to be around in October 2097, they buried a time capsule to be opened then.

Martha’s Vineyard, Massachusetts (2 Hours: 50 Minutes)

About a third of the travel to Martha’s Vineyard includes the ferry ride. However you can take your car over, so it’ll still count as a road trip with beautiful on-ocean views. Technically there are 6 towns on the island, but in a lot of ways they work together as one. With a long list of famous individuals having homes or regularly visiting the island, including 3 former presidents, it has been nicknamed “Hollywood East.”

Killington, Vermont (2 Hours: 47 Minutes)

Chartered in 1761, and then renamed in 1999, Killington is home to the Killington Ski Report. The largest ski area in the Eastern US. Nicknamed the “Beast of the East,” the resort has 155 trails, 21 lifts, and just over 1,500 acres to ski. With the town having less than 2,000 permanent residents, skiing is the only reason to trek out to Killington.

Killington, Vermont is also a great place to visit in the fall for all the incredible fall foliage . Enjoy driving around Vermont to see everything the state has to offer.

Albany, New York (2 Hours: 43 Minutes)

The capital of the state of New York since 1797 when the US was formed. It is also the longest continuously charted city in the United States, starting in 1686. As a major city, it has all of the attractions of a city, without all of the people. 70% of their permanent population comes from the 7 colleges and universities within Albany, including the nationally recognized SUNY Albany.

Road Trip Destinations within 2 hours from Boston?

Newport, rhode island (2 hours: 4 minutes).

Known as the Sailing Capital of the world, Newport has several big claims to fame in the sports arena. The first U.S. National Tennis Championships, the second is the home of the National Sailing Hall of Fame and finally, the International Tennis Hall of Fame. They also have a close relationship with the navy, housing the Naval War College and Naval Undersea Warfare Center since 1861.

Berkshire, Massachusetts (2 Hours: 2 Minutes)

In Massachusetts, when you want to get away to somewhere quiet and relaxing, it’s often a day trip to the Berkshires. With lots of history, good food, shopping, and lots of outside activities, it’s a great escape from the city. Additionally it has so many cute hotels and AirBnBs for a relaxing getaway.

Enjoy some more great small towns in Massachusetts here !

Kennebunkport, Maine (1 Hour: 45 Minutes)

Originally settled in 1653 as part of Massachusetts, Kennebunkport is another beautiful coastal town. Along with the numerous beachfront hotels, it is also the summer home of former presidents George H. W. Bush and George W. Bush. With lots of summer activities and miles of beaches, it’s a popular tourist destination.

Portland, Maine (1 Hour: 41 Minutes)

The largest city in Maine, with ocean views and vibrant nightlife. Old Port hosts dozens of restaurants and bars all within walking distance of each other, it’s known as a destination for foodies. Additionally there’s two big universities, a baseball stadium, a basketball court, an observatory, and a large few large performance venues. They have something for everybody.

Providence, Rhode Island (1 Hour: 41 Minutes)

The capital and largest city in Rhode Island was settled in 1636. It was also one of the original thirteen colonies. Now it’s a growing city with eight hospitals, eight institutions of higher learning, several museums, the oldest baptist church in America, and a zoo. Of course, you can’t forget the roadside attraction, Nibbles Woodaway , the world’s largest artificial bug atop the Big Blue Solutions building.

Ogunquit, Maine (1 Hour: 31 Minutes)

Another oceanside town settled in 1641, it served as the first sawmill in the United States and grew into a shipbuilding town. Famous for fishing, it currently has a Museum of American Art, a playhouse, and a couple of beaches. With a population of less than 2,000 year-round residents, it’s one of the least populated towns on our list.

Road Trip Destinations about an hour from Boston?

Cape cod, massachusetts (1 hour: 15 minutes).

A peninsula extending into the Atlantic Ocean, it includes 15 unique towns. It’s broken into Upper Cape, Lower Cape, and Mid-Cape. If you like seafood or lighthouses (there are 19 of them), this is a beautiful drive with friendly locals.

Wachusetts, Massachusetts (1 Hour: 5 Minutes)

Another great ski destination, and one of the ones listed in our Best Skiing in New England article . With 100% snowmaking capacity and night skiing on most trails, it’s a great local mountain. In addition to the ski resort, there is a Great Wolf Lodge located nearby with indoor pools and water parks.

Want more great ideas for ski resorts in New England? See our article about the Best Skiing in New England .

Hampton, New Hampshire (1 Hour: 3 Minutes)

Heading north from Boston, you’ll the little town of Hampton, NH. While over 2,000 of the homes in town are for “seasonal or recreational use,” meaning that they have lots of rental housing if you wanted to spend the night. They are most popular with summer tourists, with a beach, a state park, and a music venue.

Rockport, Massachusetts (55 Minutes)

One of our favorite places to visit and walk around downtown. Founded in 1840, it’s right on the coast and has beautiful views of the ocean. With a very walkable downtown (and even colored routes marked out on the sidewalk), and lots of cute local stores, you could spend hours and not run out of things to see.

Worcester, Massachusetts (51 Minutes)

The second most populated city in New England, Worcester also has the second largest art museum in New England and the oldest pipe band in the US. It’s also home to Worcester Polytechnic Institute, Worcester State University, and College of the Holy Cross, one of the oldest Catholic colleges in America, and 6 other universities. Additionally it has all the activities of a big city without the crowded streets.

Plymouth, Massachusetts (50 Minutes)

Home of Plymouth Rock , where the pilgrims landed in 1620, making it one of the oldest colonies in the United States. Also the home of America’s first thanksgiving feast, this is a town that embraces its history at the start of our country.

Salem, Massachusetts (40 Minutes)

First settled in 1626 by English Colonists, Salem was a major seaport for the North Shore area. Most famously known for the Salem Witch Trials, they take Halloween and all things witches very seriously. They seem to celebrate Halloween all year long , with year-round haunted house tours, psychic conventions, and lots of ghost stories.

Foxborough, Massachusetts (39 Minutes)

Once home to the world’s largest straw hat factory, it’s now known most commonly as the location of the Gillette Stadium. Gillette Stadium is home to the New England Patriots Football team, but is also a FIFA World Cup location in 2026. Outside of the stadium is primarily support businesses, such as the restaurants and shops in The Patriot Place Shopping Plaza.

Enjoy some fun Boston-specific events like Boston First Night or Boston Marathon .

How Far Is It From Boston To The Maine Border?

From downtown Boston to the Maine border is just about an hour, making it a very easy day trip. Maine has some beautiful ocean views and island escapes. If you wanted to continue your drive through Maine, see our Maine Category for some great ideas. If you’re trying to decide between visiting Maine or New Hampshire though, there are definitely pros and cons to both.

How Far Is It From Boston To The New York Border?

From downtown Boston to the New York border is about 3.5 hours, or 183 miles, making it a very easy day trip. New York, Long Island, and New Jersey are all great locations for all of the activities of the big cities.

Your Perfect New England Road Trip Itinerary: Plan a Road Trip From Boston

May 6, 2021

Start with a road trip from Boston.  Mix lighthouses, whaling ports and clam chowder with the origins of modern America with this New England road trip itinerary. By the end, America may seem older but you’ll feel younger.  Here’s how to make it happen.

Table of Contents

The Perfect New England Road Trip From boston

New england road trip itinerary map.

A Two Week New England Road Trip Itinerary

This New England road trip itinerary follows our well-researched plans. We spent two weeks driving around Massachusetts, spending a few days in Boston and then looping through three key areas: Salem and Cape Ann to the north of Boston, historic Plymouth, Cape Cod, Martha’s Vineyard and Nantucket to the south and then inland to endless tree-lined roads in the Berkshires.

Separate stories of the people we met and the stories we uncovered will come elsewhere on the lab ( see the USA section here ), along with poetry, whimsy and the story of the invention of the first ever fried clams.

Whether you’re at the dreaming, planning or booking side of things, I present you with a nuts and bolts New England road trip itinerary to help you plan your perfect road trip from Boston.

From Massachusetts to Manhattan and Brooklyn

Another great idea is to extend your Massachusetts road trip into New York State. Brooklyn is one of the most densely populated urban areas in the world and intriguingly diverse: over 60 languages spoken in the area.

It’s also known for being an artistic hub, and a great alternative place to stay to cross the bridge and explore Manhattan. Here’s a lovely example of a boutique hotel in Brooklyn to add to your road trip plans.

Boston: Days 1-3

Spend a few days in Boston recovering from jet lag and enjoying this historic, thriving, curious, famous city often overshadowed by nearby Manhattan.

• Recommended reading: Things to do in Boston and beyond .

Salem and Cape Ann: Days 3-5

The first stop on this New England road trip itinerary has history and white picket fences written all over it.

Salem’s most famous role was as the heart of the infamous Witch Trials of 1692, brought to 20 th century audiences (and schoolrooms) through Arthur Miller’s The Crucible and a subsequent performance by Winona Ryder.

The first part of the Salem Witch Museum explores story of the original trial. But even more interesting than that is the second section. Here, the conversation moves to the idea of a “witch hunt” and the process through which society mistrusts and demonises “outsiders.”

The Salem Witch Museum really isn’t suitable for children under 8. It’s dark with screaming, animated, figures and a human-size devil, so it’s the one thing I’d recommend families take in turns or skip.

Cape Ann is a gorgeously rural, windswept place with pebbly-sand beaches that lift the soul at dawn. What’s even better? You won’t find many tourists here, at least not from outside America.

As a result, a visit to Cape Ann is all about taking in nature and local customs and really slowing down.

As so many events are weather dependent (and you rarely need to book) I’d advise you look at a map and mix and match from the following. You should be able to fit everything in within a couple of days.

Watch Sunset at Pigeon Cove

This gorgeous spot has been entertaining guests since the 1850s when William Norwood set up a tavern carriage traders. In its time, it attracted literary greats like Ralph Waldo Emerson (“Trust thyself”) and Henry David Thoreau so you can feel englightened as you dine (toddler included.)

• Book your spot at Emerson Inn here.

Spend the Day at Appleton Farms

Nine generations of Appletons have worked on Appleton farm , amid crumbling stone walls and one of the earliest American dreams. That makes it one of the oldest continuously operating farms in America.

Today, it’s part of the Trustees for Reservations Group (a kind of American National Trust.) Overall, Appleton aims to bring the wholesome, heritage parts of farming to city slickers and those who want to get involved.

It spreads over 1000 glorious acres of rolling grasslands and maple trees, like scenes from Jed Bartlet in New Hampshire in the West Wing. But it’s not just pretty for the tourists.

It’s a working farm and you can visit livestock, hike for hours or visit the historic farmhouse.

Catch the afternoon milking of the Jersey cows at 4:00, say hello to the chickens, goats and sheep at any time. And if you’re lucky, catch a cheese-making demonstration at the creamery.

Visit the Singing Beach

Manchester’s Singing Beach has a poetic name for a poetic place. The sea may not actually sing (it’s more like a whistle) but its sense of peace was one of the highlights of this New England road trip itinerary.

Go for Dinner or Cocktails at the 1606 Restaurant, the Beauport Hotel

Join the much-feted East Coast Elite in the glory days of shipping by dining at 1606 Restaurant at the Beauport Hotel. The restaurant overlooks the sea, with a luxurious nautical theme of polished wood, white walls and knotted rope. Seduced by the gentle live music, it’s easy to believe that you too could run for office one day…

Visit the Birthplace of Fried Clams

At the other end of the spectrum is Woodman’s of Essex , the self-proclaimed “home of the fried clam.”

It’s a lovely story told by lovely people. In 1916, Lawrence “Chubby” Woodman, at the suggestion (near dare?) of a friend, decided to fry some clams ahead of the national July 4 th celebrations. Five generations and over 100 years later, the clam shack is still going strong, and the legacy of the fried clam has spread across New England.

Here, you grab a seat with friends and tuck in to a range of fried fare, including the state’s iconic clambake and the fresh lobster for which New England is so well known.

Where to Stay in Cape Ann

We stayed at the Castle Manor Inn , a lovingly restored Victorian Inn just made for flowery dresses and Instagram. It’s situated inland, with soothing green gardens and that mix of grandeur and homeliness that buildings of that era exude.

While atmospheric, it’s probably not the best choice for young children as there’s no crib or soundproofing. But, if you’re travelling as a couple, it’s romantic, and if solo, a good place to chat over breakfast on the narrow terrace. And the staff couldn’t be friendlier.

Plymouth, Cape Cod and the Islands: Days 5-11

Now it’s time to visit all those places you’ve heard about in half-whispered dreams, novels, schoolrooms, history books and anything that probes into the life of J.F.K. Plymouth, Cape Cod and the islands.

Plymouth is where America began. Kinda.

It is where the pilgrims settled (they landed at Provincetown), and it remains the oldest continuously inhabited settlement in the United States founded by Europeans. Others may have got there first, but this was the only one to last.

Its history is fascinating and complex; its layout restfully small. It’s a walkable, beautiful grid of artsy coffee shops, bobbing boats and impressive, historic brick buildings.

But before you get there, allow your New England road trip itinerary to stop off at World’s End in Hingham and the cranberry bogs along the way.

World’s End

This unexpected wilderness between Boston and Plymouth offers a chance to get back in touch with nature and see views that haven’t changed for centuries.

Managed by the Trustees (the same ones who manage the Appleton farms), World’s End involves over 250 acres of tree-lined avenues, rocky shores, steep hills and wild grass.

Look one way to see Boston, its skyline painted in faint, pastel colours. Look the other to see a Nordic fishing village which turns out to be the New England coastline.While the buildings of New England may be old in US terms, this place is even older.

Linked to the retreat of the same glacier that led to Boston Harbor, the salt marshes and spoon shaped hills (or drumlins) look the same now as they did thousands and thousands of years ago.

The Trustees hold concerts here on a summer’s day, but, even if grey clouds roll in, a stride between the granite ledges, red cedars and blueberry thickets make the perfect exercise break on a road trip from Boston.

The Cranberry Bogs

Yes, when I heard about cranberry bogs I wasn’t that impressed.

Yes, when I saw a photo, I completely changed my mind.

Cranberries are big business in New England, with U.S. Farmers harvesting approximately 40,000 acres of cranberries each year. What makes this farming industry so much more interesting than the rest are the shimmer of the cranberry bogs come harvest time.

Full of bright red berries as far as the eye can see, farmers flood the bogs with enough water to cover the vines that carry the berries. They then use water reels to knock the fruit off and collect them with conveyors or pumps.

Alas, for international visitors, the season is short, running from approximately mid-September to early-November each year.

We stopped off at Mayflower Cranberries LLC (call ahead if you wish to do the same) in Plympton, Massachusetts to speak to owner Jeff LaFleur.

An amiable, passionate man, LaFleur has taken cranberry farming to the next level. His 112-acre farm  has 236 acres of active cranberry bogs and he’s also a grower-owner for Ocean Spray Cranberries. As an aside, I had assumed that this was a big, faceless, awful corporation before this visit, but it’s actually a pretty decent co-op that benefits small farms and keeps them in trade. Jeff is a fan!

In Plymouth, you can indulge in as much or as little history as you like. Unless you’re particularly keen, though, one full day is probably enough. Spend the day from Boston to Plymouth stopping off at World’s End and the cranberries, and then give yourself one full day in Plymouth itself before driving on to the Cape.

The Plimouth Plantation is a little way out of town, but everything else is easily walkable, and it’s really the best way to get a taste of the place.

Plymouth Rock is New England’s most visited rock (drawing in more than 1million visitors each year).

This historical landmark signifies the place where the Mayflower pilgrims began Plymouth Colony, which is essentially the first permanent European settlement in New England.

You’ll find Plymouth Rock in the peaceful Pilgrim Memorial State Park on the shore of Plymouth Harbor.

The Plimouth Plantation

The open-air museum that is the Plimouth Plantation really turns the traditional idea of the American thanksgiving around.

Two villages co-exist:

• the Wampanoag settlement with trailing smoke, simmering cauldrons, feathers, paints and spears.
• the pilgrim settlement, where actors have British accents and talk about their journey from Leiden in Holland where they were granted asylum before they left ”to find the new world.”

A Tale of Two Sides

From a fraught narrative, the Plantation showcases both sides of the American story without passing judgement. Leave at least a full afternoon to really make the most of it.

Where to Eat in Plymouth

• Kiskadee Coffee Company – for local art, simple snacks and, well, good coffee.
• The Water Street Café – head to this diner for an all American breakfast you’ll never forget. Order crunchy French toast and consume more calories in one sitting than you even do at Christmas. Guilty. Delicious. Fun.
• Dillon’s Local – we enjoyed this so much, we went back twice. ;-)  Cosy, yet hipster eatery with classics like New England clam chowder and more modern arugula grilled peach salad.

Where to Stay in Plymouth

We stayed at the John Carver Inn & Spa , right within walking distance of town.

It’s a curious spot, with a mix of themes and styles, but rooms are spacious and well stocked. There’s a fantastically outrageous swimming pool with a full size replica of the Mayflower (with a bit of artistic license!).

After you check out, it’s time to grab your swimwear and prepare to head to the Cape…

Cape Cod and the Islands

This is the section of a Boston road trip that takes the most planning before you go.

But, oh my, is it worth it.

There is a spirit around the Cape that is simply unique. The curling tip of land that tickles history, the roar of the waves and the sharks that circle around. The taste of the air and the stick of the salt and the sense that adventure and the open world wait just around the corner.

And truthfully? We should have planned a little better and given ourselves more time. Not because there are so many things to do (there aren’t really), but because this is a place to slow down and not really think about things to do.

• Recommended reading: how to plan a road trip by yourself

Fitting the Pieces Together For Cape Cod and the Islands

• Station yourself in Hyannis, the hub of the Cape. While not the prettiest part, that’s a bit like saying Monet’s poppies aren’t as pretty as his waterlilies. It’s also close to the ferry port, making those connections far easier.
• Don’t take your car to Nantucket.
• I know I keep mentioning this,  but it’s important. Parking is tricky there and getting the car onto the ferry is even trickier.
• I’ll write more about these areas separately, but for now, here’s the key information to help you plan your visit.

The Cape Cod National Seashore

Managed by the National Parks Service, the Cape Cod National Seashore area cuddles along the curve of the Cape, flanked only by majestic Atlantic pine, sand and the odd shark.

Arrive early as parking is limited and expensive so it makes sense to stop for a while.

Glossy, well-heeled Chatham is a delight to walk around in between its sassy book shops, art galleries and antique shops. At the “elbow” of Cape Cod, this is the point where Nantucket Sound and the Atlantic Ocean meet.

There’s easy access to a windswept sandy beach with a lighthouse that dates back to 1878. And if you’re in luck, you can catch the annual shark art festival:

Where to Eat in Cape Cod

Twenty-Eight Atlantic at Wequassett Resort  –  Fine dining with full views of the sea. Look out for the ash-roasted cod loin and Chatham shellfish company oysters.

The children’s menu also comes as a sail on a wooden boat and table lights come inside hollowed sea urchins.

Twenty-eight Atlantic enjoys the highest ratings on Cape Cod from Forbes, AAA, and Zagat and it’s easy to see why.

Where to Stay in Hyannis

We stayed at the Anchor In , a convenient spot in Hyannis with spacious, light rooms, well-informed staff and a small outdoor pool with a view of the marina. A cosy “old New World” library serves breakfast and drinks through the day as well.

How to Get From Hyannis to Nantucket

We travelled with Hy-line cruises. The journey is short (136 minutes) but leave plenty of time to board and book your ticket in advance.

There’s a small café on board and an easy chance to walk around for toddlers.

Oh, how I loved Nantucket. I Really, really loved the place.

This small island, only 30 miles across, seems to tell the story of human innovation and reinvention through a series of picturesque beaches, stylish place to stay and chic spots to eat.

Architecturally, little has changed from the 17 th century whaling hey days, all wooden slatted town houses and white columned porches.

Once it was one of the wealthiest spots in the world, thanks to its whaling industry.

Today it welcomes tourists and grapples first hand with balancing the past, the future, sustainable tourism and identity. Nearly 40% of Nantucket is protected for conservation and the island is now a National Historic District to boot.

All of which sounds far too serious for what is, essentially, a gentrified beach resort. But that’s what makes it so interesting.

Visit the   Whaling Museum to uncover a striking, poignant, provocative and unapologetic look at the realities of the whaling industry and why it was so important to the world at that time.

Finding the Beach

Brant Point is a short and easy walk from Nantucket’s centre for an iconic lighthouse shot and scuff in the sand. Watch the ferries glide in and think back to the whaling past. Don’t try to swim, though. Currents here are far too strong.

The Children’s Beach is even closer to town with a playground and kids activities on in the summer.

For further beaches and exploration, hire a bike and cycle away!

Where to Stay in Nantucket

We stayed at 76 Main Hotel. This gorgeous little bolthole forms part of a small local chain, called/run by Lark Hotels.

Stylish inside and out, rooms are small but deliciously designed.

There’s even a private firepit to help you embrace another Nantucket custom: melting marshmallows, biscuits and chocolate to build your own s’mores…

Martha’s Vineyard

After Nantucket, Martha’s Vineyard seems enormous and urban. But of course, in reality she’s only 25 miles across with a population of around 17,000.

Her villages have different character, but you’ll find a key blend of summer holidays and New England in each.

You can catch the ferry from Hyannis but we drove from Hyannis and picked up the Steamship Authority ferry from Woods Hole to make the next part of the journey a little easier.

Arrive in good time to queue with your car but again, there’s a café and room to walk around when on board. And some spectacular views as you approach the island.

What to Do in Martha’s Vineyard

A trip to Martha’s Vineyard forms an essential part of any New England road trip itinerary. Here are the highlights:

• Look out for Murdick’s Fudge
• Visit Tuck & Holand Metal Sculptors at the Vineyard Haven Gallery to meet the man who makes weather vanes for the stars (Steven Spielberg has a velociprator made on this very island.)
• Feel the salt in your lungs and the wind in your hair on Martha’s sandy beaches.
• Pay a quick visit to the pastel-pretty gingerbread cottages in Oak Bluffs.
• See the wealth of the whaling captains in Edgartown, Martha’s first colonial settlement, through their Greek revival mansions.
• Give Mad Martha’s ice cream a good licking. With a fun name like that, you may as well try one.

Where to Stay in Martha’s Vineyard

The Winnetu is the kind of place I’d love to stay at all week for one of those relax-and-forget-about-the-world holidays – with children.

It’s unusual in that it is designed with families in mind – and yet it still manages to be pleasing to the eye for adults!

Rooms have decent high chairs, cots and mini self-catering facilities but with a beautiful, New England design that appeals to adults.

The Dunes Restaurant introduced a new concept to me: adult dining with a children’s play area within the restaurant (if you don’t have kids, don’t fear, there is an adults-only section.)

The hotel’s outdoor pool is set in spacious grounds with a lifeguard and towel service and seemed surprisingly, blissfully empty for the most part. The great, green grounds led to the ocean at South Beach where it was too blustery for us to go in but seemed majestic in its beauty.

From Martha’s Vineyard to the Berkshires and Around: Days 11-14

Get ready to welcome manicured, college campus America, with a side stop into the edgier Springfield, home to the Dr. Seuss Museum and the man himself. In fact, the key draw to this region (for me) was the “Iconic Illustrators Trail” – an intriguing journey through different areas of New England, each with amazing images.

From Martha’s Vineyard to Springfield

We took the ferry from Martha’s Vineyard to Woods Hole as it shortens the driving time as compared to a return ticket to Hyannis. Check which makes the most sense for you.

Springfield was a surprising stop on this New England road trip itinerary. It broke the classic “New England” style and probably deserved a little more exploration.

Local boy Dr. Seuss (real name Theodor Geisel, ) grew up here amid the thriving inner-city medley of life with newly arrived immigrants from around the world. And The Amazing World of Dr. Seuss Museum shows how that background developed into a world-famous career through personal artefacts, photographs and handwritten notes.

However, the real scene-stealer is the whimsical area downstairs, where characters like the Lorax greet you in life-size form. It is aimed at and perfect for children.

Where to Stay in Springfield

We stayed at the Tower Square Hotel , a tall, slick city affair with a suite that had a separate kitchen that would have been a godsend if we’d still been weaning (it was still pretty good as we could have some family time after baby lab went to sleep in our room.)

There’s a pool with a sporty feel on one floor and an all-American breakfast available in the basement. Concierge parking and a 24-hour reception desk marked a return to city life after the blue-and-white laid-back feel of the islands.

Where to Eat in Springfield

Adolfo’s, just around the corner from the Tower Square Hotel , offers tasty, unpretentious Italian food with a local twist. Look out for the owner’s legacy on the walls…

Springfield to Amherst

What’s the reason to stop off in Amherst? Why, the Hungry Caterpillar Museum .

Of course, its real name is the Eric Carle Museum of Picture Book Art and it celebrates the work of illustrators across the world. The library arranges books by illustrator rather than author and there’s a huge room dedicated to getting arty and involved with crafts.

Local Flavours in Amherst

Just down the road is the Atkins Farms Country Market , a supermarket come delicatessen come restaurant that showcases the local farming produce. And it’s amazingly tasty.

Perfect for stocking up for picnics or dropping in for a bite to eat.

From Amherst to Northampton

This short journey only takes 20 minutes. Check in and enjoy the evening. There’s more exploring to do tomorrow.

Where to Stay in Northampton

We stayed at  The Hotel Northampton . Looking for a taste of American history? This is it.

Eleanor Roosevelt, Jenny Lind, Herbert Hoover, Calvin Coolidge, Dwight Eisenhower, John F. Kennedy, and Richard Nixon all dined in the hotel’s restaurant,  Wiggins Tavern , in Northampton.

Rooms are moderate sized and blissfully quiet, with cots on request and a breakfast to make Americans proud.

There’s also a fantastic toy shop across the street, with the loveliest staff. They found us lightweight building blocks that stick together without glue. Perfect for travelling. Just as an aside ;-)

Where to Eat in Northampton

Bistro Les Gras – It’s a gorgeous sunset walk through Northampton to reach Bistro Les Gras, where locals dine for special occasions (they came, they chatted, they told us.)

Amid low lights and American-French charm, try the wild gulf shrimp and lemon tart. If you have a wriggly toddler with you, it’s easy to pop out and visit the live music opposite.

The Normal Rockwell Museum

The Norman Rockwell Museum tells not only the story of the world famous artist but also, in a way, the story of 20 th century America as well.

Photos, paintings, and the painstakingly relocated office of the man himself offer an insight into an America that laid the foundation for the one of today.

Tanglewood & Lenox

Tanglewood is a place to get your music groove on, as long as there’s something on. The 210 acres of the Tanglewood estate  were given to the Boston Symphony Orchestra in 1936 by Mary Aspinwall Tappan and the result is half stately home gardens, half rock and roll concert venue.

Even if there’s not a concert going on, you can get in and look around.

Where to Eat Near Tanglewood

Lenox is another quintessential small New England town, with boutique art shops, white fences and cute places to eat.

Tanglewood to Deerfield

The last stop before returning to the hubbub of either Boston or its international airport is the leafy, quiet village of Deerfield. Here, historic mansions rise into the sky with the trees in this 18 th century village that simply froze in time.

Where to Stay in Deerfield

Book in advance to stay at the Deerfield Inn , right in the heart of the historic part of Deerfield. Guest rooms wear period florals, lamps and bedspreads and the dark wooden writing desks seem from another age.

Deerfield to Boston

And so, this rather epic Massachusetts road trip comes to an end.

But there’s one last stop en route to the airport: Louisa May Alcott’s house .

The author of the international bestseller published in 1868, lived here with her three sisters and parents on the outskirts of the small town of Concord.

It’s a heart-fluttering stop for literature but it also shines an interesting spotlight on society in New England at the time.

How to Make It Happen

Driving is easy in Massachusetts, even if you’re used to driving on the left. Signs are clear, fuel is easily found and all the signs are in English.

America is a country built on transport, and the love of the automobile runs deep. It is more or less expected that you’ll drive everywhere and, as a result, parking is plentiful and cheap (and public transport tends to be sporadic and awkward.) It’s one of the reasons why this New England Road Trip itinerary works so well!

Explore Our Road Trip Planner & Toolkit

Designed for those who love to travel but who hate spreadsheets, our Road Trip Planner & Toolkit system shows you a bulletproof formula for getting organised in half the time. Plus, it includes the one innocent mistake that even seasoned travellers make.

The key exceptions to this are in Boston (a big, old city where walking and public transport will serve you best) and the island of Nantucket (where cars are virtually forbidden.)

Access to the beaches at Cape Cod also require hefty parking fees as the place is so popular and the villages so small.

By and large, though, Massachusetts, like so much of America, is built for a fly-drive holiday.

Where and When to Pick Up Your Car

Spend a few days in Boston, soaking up the accent, the red-brown leafy streets, the education and the arty brunches.

Then pick up your car either at the airport or at one of the centres in town. Unlike most cities, Boston Logan International is quick and easy to get to, so if you plan on flying straight out at the end of the trip, then it’s cheaper and easier to drop off at the airport and go.

Car Hire With Perks: Hertz Gold

We rented a car through Hertz . The booking and collection process was simple, but what makes the service even better is that they have an  American Road Trip Planner . It makes drafting itineraries so much easier.

It’s perhaps not a great way of calming wanderlust, but it does mean that you can quickly plan another trip; an ideal way to beat the travel blues in my opinion

If you register with  Hertz Gold Plus Rewards BEFORE you make your reservation you receive better deals, the chance to skip the queues and to use the Gold Plus Rewards counter. It’s free to register and only takes 60 seconds, so it’s worth doing.

What You Need to Plan in Advance

If you really have your heart set on something in particular then it makes sense to book it as soon as you can.

For me, though, most of the joy of travel involves a certain level of spontaneity and exploration, to follow where I want to go and (excuse the cheese) allow the essence of the place to appear at its own pace.

That said…in Massachusetts there are some things you really need to book in advance.

• Ferries and accommodation on the islands of Martha’s Vineyard and Nantucket are often in short supply, with a fixed number of nights bookings and timetables that you need to stick to.
• Leave your car behind as you head for Nantucket (leave plenty of time to find a parking space in Hyannis as it’s a bit of a scrum. Enterprising householders nearby charge a hefty fee to let you use their driveway.)
• Boston can also book up quickly and so the sooner you can nail down your accommodation and car hire there, the better.

Lock these down first then work backwards from there.

Booking Flights to Boston

Our partner for this trip, Norwegian, has increased services to Boston with a daily non stop service between London Gatwick and Boston Airport. The flights are operated by a fleet of brand new Boeing 787 Dreamliner aircraft with two cabins in premium and economy.

Fares start from £155 one way / £259 return in economy and £415 one way / £745 return in premium, including all taxes and charges.

To book visit  www.norwegian.com/uk  or call 0330 828 0854

Wifi On the Road

It would be optimistic and slightly romantic to think that mobile internet isn’t needed for a road trip. It’s near essential for navigation, for looking up nearby restaurants and opening times and great for contacting people back home.

Mobile internet can be expensive, though, not to mention a pain to set up if you have to get a SIM card at the airport.

We rented a mobile wifi device (aka a MiFi) on this trip. It’s really convenient for family trips because everyone can join a single device instead of replacing all your SIM cards. You also get to use your original phone number so you don’t have to worry about the logistics of checking two numbers or letting loved ones back home know.

Mobile Internet from Cellhire

Cellhire is a world leader in mobile communications , allowing travellers to stay connected all over the world. The USA MiFi is one of Cellhire’s most popular products. It’s well-loved for its instant data connectivity abroad, super-fast 4G speeds and its 5GB and 10GB bundles. The USA MiFi starts at as little as £50 a month.

Should I Travel to Massachusetts with Children?

Yes, a resounding, yes! People are friendly, polite, services work, healthcare is great and driving and parking is easy. This is America, after all. :)

However, while Florida and Louisiana seemed enthralled by our smallest travel companion, some (only some) areas we visited in Massachusetts seemed a little more reserved.

We were warmly welcomed at fine dining establishments, museums, on flights and in hotels but I’d just say that the difference between Massachusetts and the South was like the UK and the Med. Children are  adored  in the south, welcomed further north.

Adding More States To Your New England Road Trip Itinerary

This New England road trip itinerary focuses on Massachusetts, without apology. It’s aimed to maximise your time out exploring if you only have two weeks available, which is the standard setup for travellers from the UK.

More East Coast Road Trip Routes Along the New England States

However, there is so much more to New England than Massachusetts.  By definition, it includes six states rather than one, and so add the names Maine, Vermont, Connecticut, New Hampshire and Rhode Island to your New England list.

Typically, autumn or fall is the time to make your way through these states, “leaf peeping” as you go. The colours are extraordinary, the maple syrup refreshingly sweet. There’s also winter sports and skiing in Vermont come winter and long hikes along the east coast for summer road trips. In my opinion, it’s better to take it slow and explore one area rather than trying to cram everything in. But to give you a few more ideas, here are some other New England road trips that explore the other states.

More New England Road Trip Itineraries

• Rhode Island – the state so small, you can drive across it in an hour. However, here are some Rhode Island Road Trip Itineraries that take in lighthouses, natural wonders and small villages, as well as Block Island.
• Here’s a road trip itinerary for Maine, taking in popular spots Portland, Camden and Park Loop Road just south of Bar Harbor in the Acadia National Park.
• Waterfalls, skiing and wine routes feature in these Connecticut road trip itineraries through the Litchfield Hills and New Haven.
• Explore the great outdoors of the Green Mountain State with these road trip itineraries for Vermont.
• And last but not least, drive around New Hampshire’s  Kancamagus Highway to the White Mountain National Forest. 

Keen to travel further afield but unsure where to go? Check out our guide to choosing between Los Angeles and Miami .

Beyond the East Coast: Other American Road Trip Itineraries

New orleans, louisiana.

Let the good times roll with this fascinating and fun road trip from New Orleans. Explore the less well known parts of Louisiana and learn more about America.

Florida, West Coast Itinerary

Flit from the beach to sweeping cool art museums with this Florida west coast road trip itinerary. Discover sleepy villages and a world away from the resorts.

The Great River Road, Louisiana

Explore the grandeur and the horror of plantation life with this road trip itinerary along the Great River Road in Louisiana. Then cool off amid the marshmallow in one of New Orleans’ best swamp tours.

Plus, check out how to plan your San Francisco to Santa Barbara road trip here.

Road Trip Planning Tools and Essentials

We love, love, love a good road trip here on Inside the Travel Lab and have driven solo, as a couple, a family and with friends all over the world. It’s such a great way to get off the beaten track and to feel the sense of freedom and exploration if only for a short while.

That’s why we’ve put together a series of tools and resources to help you plan your New England road trip.

For starters, don’t miss the 53 Road Trip Essentials checklist that covers what you need to pack. Then, sign up for our free road trip training sessions, a series of three videos to help you avoid the mistakes that I’ve made.

Last, but by no means least, check out our Road Trip Planner & Toolkit. It’s a revolutionary way to organise and plan out your road trip, without spreadsheets, lost scraps of paper, headaches and overwhelm. You can check that out here.

Anything else I can help you with? Just let me know!

Disclosure – This trip was made up of some self-funded aspects and a mixture of paid/unpaid partnerships with Hertz, Visit Massachusetts, Norwegian, and Cellhire. As ever, all opinions remain my own. Otherwise, what is the point?!

If you book or buy through links on this page, we may earn a small commission at no extra cost to you. Cheers!

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17 Fun Weekend Getaways from Boston

Boston is truly one of the best cities in the United States –and that’s even before you consider just how many incredible weekend getaways from Boston there are!

As the largest city in historic New England, Boston is filled with some of the most amazing restaurants and photo spots east of the Mississippi River.

However, everyone needs a getaway sometimes, and no matter what your travel style, there are enough short trips from Boston to add to your bucket list, that you can stay busy in the northeast for years!

Some places on this list can be visited utilizing public transportation, such as the Peter Pan bus, Greyhound bus, or Amtrak.

For the most part, though, you will need to either have your own car or rent a car for these weekend trips from Boston.

Here are the best weekend getaways from Boston–plus some tips on how to plan your trip!

Note : This blog post was written for Our Escape Clause by former Boston resident Krystianna of Volumes & Voyages . Thanks for joining us, Krystianna!

Table of Contents

Boston Weekend Getaway Travel Tips

The best cities for weekend getaways from boston, best small-town weekend trips from boston, nature-focused boston weekend getaways.

Some links in this post may be affiliate links. If you make a purchase through one of these links, we may earn a small commission at no extra cost to you. Please see our disclosure policy for more detail.

Before hitting the open road, here are some tips to keep in mind when planning a short getaway from Boston!

Pack for all types of weather.

New England is notorious for having strange and unpredictable weather.

Sometimes, there is a random snow day in May, and sometimes it will randomly be really warm in the middle of November.

For the most part, you’ll want to pack for the season, but don’t be afraid to also pack layers because you genuinely don’t know what you’re going to get !

Be prepared to make stops along the way!

There are so many great places to visit in the northeast, and you will most likely pass by some of these spots along your drive.

Try to plan on pulling off at least a few times during your ride to or from your destination if you’re driving a car.

Especially if you’re heading up to Vermont or Maine, you’re going to pass by some epic viewpoints driving from Boston.

Rental car prices can vary dramatically depending on pickup location.

Don’t just rent from the first rental car place that you find.

Instead, be sure to check out other rental car options in the area , including Boston’s suburbs.

You might be surprised at the deals you’ll be able to find by heading outside the historic center!

For browsing, we recommend shopping with Discover Cars !

They’ll compare prices and inclusions from multiple brands to ensure you’re getting the best deal for your trip.

Compare rental car prices and inclusions with Discover Cars today!

Portland, Maine

Nestled on the coast of southern Maine, Portland is one of the easiest weekend getaways from Boston and is a classic New England getaway.

While you’re there, be sure to stroll around the Old Port, admire Portland from above at the Portland Observatory, snap photos at the Portland Bug Light, tour the beautiful Victoria Mansion, and visit a few of Portland’s famous breweries.

And, of course, you can’t visit Portland without heading out to John Williams Park and admiring the famous Portland Head Light for yourself!

Distance from Boston

1 hour, 45 minutes by car or 2 hours, 30 minutes by train.

How to Get to Portland from Boston

While driving is the easiest way to visit Portland (you’ll have more options for exploring and day trips while you’re there), there are also direct trains between Portland and Boston, making this one of the best Boston weekend trips for travelers who don’t want to drive.

Where to Stay in Portland

• The Francis: This hotel is a historic landmark in the Bramhall neighborhood, near the Art District, and has a fabulous on-site spa. Perfect for a weekend relaxing.
• Best Bower: Simple, clean, and classic with all the cozy luxuries you could wish for from your weekend trip.

New York, New York

New York City is America’s most popular city for a good reason: it’s loaded with great things to do!

Absolute must-sees during a weekend in New York City include Central Park, the Statue of Liberty, Times Square, and the Empire State Building.

Fans of museums and history should also opt to visit the Metropolitan Museum of Art or the Modern Museum of Art.

If you’re lucky enough to be visiting during the wintertime, you absolutely must head to Rockefeller Center to see the giant Christmas tree!

The Rockettes also perform in the winter months. More local attractions like Brooklyn’s Dyker Heights Christmas lights are also worth going out of your way for!

There are lots of great neighborhoods to stay in during your weekend.

Just remember that New York City is vast, and the closer to the city center you are, the less you’ll have to spend on transportation, and New York City traffic can be horrendous .

Opt to try to stay near SoHo for its charming architecture, Greenwich Village to be in the trendy part of the city, or Brooklyn, which is known for being hipster and upbeat.

How to Get to NYC from Boston

The easiest way to get to New York City is to drive, but having a car in NYC can be a hassle!

We recommend taking the Amtrak or the Megabus from Boston’s South Station–the train is a bit more comfortable, and less likely to experience delays due to traffic (a big risk with bus travel between the two cities) but also much more expensive than taking the bus!

Where to Stay in New York City

• Omni Berkshire Place: Just 805 meters from Central Park this Manhattan hotel is a great choice for your weekend trip. Soak in the huge bathtubs and wake up to views of the NYC skyline.
• Sixty Soho: In the heart of the stylish Soho district this is a great spot for your trip. Sip cocktails on the rooftop bar and have your own New York minute.

Burlington, Vermont

Burlington is drastically different from Boston, but that’s what makes it the perfect weekend getaway spot.

This quaint, lakeside city in Vermont is the most populated part of the whole state.

However, it only has a population of 43,000 people, with the majority of citizens being college students at Champlain College and the University of Vermont.

One of the best things to do in Burlington is to go to Church Street, which is a marketplace quite like Newbury Street and Quincy Market in Boston.

It’s a beautiful cobblestone street lined with areas to shop.

Other popular spots include the Ethan Allen Homestead Museum, Waterfront Park, and the Fleming Museum of Art.

The Ben & Jerry’s Factory is only a short ride away from Burlington, so plan on taking a detour there on your way to Burlington or on your way back to Boston.

There are free tours here offered daily, and you honestly won’t want to miss it.

3 hours, 15 minutes.

How to Get to Burlington from Boston

It’s most simple to drive to Burlington using I-93 N and I-89 N.

It is possible to take an Amtrak if you have the time, but you have to make a significant detour to New York City since there isn’t a direct route to Burlington, which can take almost a day.

Where to Stay in Burlington, Vermont

• Green Mountain Suites: The perfect spot for a classic cozy Vermont trip with open fireplaces, fluffy blankets, and an onsite hot tub.
• Blind Tiger: Another gorgeous luxury option is this hotel with a stunning private garden and comfortable rooms.

Newport, Rhode Island

Just south of Boston is the gorgeous city of Newport, Rhode Island , one of the most romantic places in the USA , and a fun getaway from Boston!

It’s most famous for its large mansions that are home to many of America’s celebrities, and in many cases, date back to the Gilded Age.

One of the best activities to do here is to go on a trolley tour, which will bring you around to many of the area’s best mansions.

Other fun things to do in Newport include swimming and shopping.

There’s also the Newport Art Museum, Castle Hill Lighthouse, the Redwood Library and Athenaeum, and Brenton Point State Park.

This area is unlike many of New England’s other cities because it really doesn’t feel like a city at all!

1 hour, 20 minutes.

How to Get to Newport from Boston

It’s easiest to travel to Newport by car, but you could also hop on two buses (one from Boston to Providence and then Providence to Newport) in under 2 hours.

Where to Stay in Newport

• Ivy Lodge: Stay in a classic mansion house complete with a turret and gothic woodwork. In the heart of Newport Mansion District and less than a mile from Newport Harbor, all rooms also have fireplaces for the ultimate romantic weekend evenings.
• America’s Cup Inn: Set along a cobblestone street with gaslights, and decorated with colonial period furnishings, this is a classic New England B&B. Rooms have 4-poster mahogany beds or antique wicker furnishings.

Mystic, Connecticut

Mystic, Connecticut, is a quintessential New England town.

It’s located right on the water and is breathtaking–there are great views almost everywhere you look !

Fun places to explore include the Seaport Museum, Misquamicut State Beach, Ocean Beach Park, and the Napatree Point Conservation Area.

Honestly, if you’re looking for a small town right on the coast, then Mystic is the place for you!

1 hour, 40 minutes.

How to Get to Mystic from Boston

Driving is the simplest way to get straight to Mystic, but you could also take the Amtrak straight from South Station in Boston.

This will only take 1.5 hours!

Where to Stay in Mystic

• The Whaler’s Inn: The Mystic River Bascule is around the corner from this historic hotel in Mystic. Wake up with designer bed sheets and mattresses and enjoy an amazing breakfast before exploring Mystic.
• House of 1833: Step back in time with this charming B&B in Mystic. Packed with historical details, antiques, and quirky collectibles, this is a great choice for a weekend in Mystic.

Bennington, Vermont

The small town of Bennington, Vermont is located in the southwest corner of the small state, not far from either Vermont’s border with New York or Massachusetts.

It serves as the perfect weekend getaway because it’s so vastly different from Boston!

While there, be sure to check out some local restaurants, including Blue Benn Diner, Jensen’s, and Papa Pete’s.

There’s also a lovely brewpub called The Tap House, which is fantastic.

If you’re a fan of the outdoors, be sure to do one of the many hikes in the area, like the hike to the White Rocks.

2 hours, 50 minutes.

How to Get to Bennington from Boston

It’s easiest to drive here from Boston. It’s possible to take multiple buses, but this can turn into a whole day ordeal.

Where to Stay in Bennington

• South Shire: This lovely hotel offers a homestay environment with added hotel touches such as a hot tub and a fabulous breakfast each morning.
• Four Chimneys Inn: Housed in a mansion on an 11-acre estate with an extensive garden, this stunning property is perfect for your weekend getaway. With four-poster beds and classic furnishings throughout you will feel truly spoiled.

Manchester, Vermont

Manchester is located only 30 minutes north of Bennington, Vermont, but if possible, it is even more charming!

This town is historic and is filled with some of the most beautiful buildings in all of Vermont, and is also a popular place to go shopping.

Be sure to check out the Manchester luxury outlet shops and also the Northshire Bookstore.

Similar to Bennington, there are a few hikes in the area that are worth doing, and these ones are a lot less strenuous than other hikes in southern Vermont. 

How to Get to Manchester from Boston

Driving is the only realistic way to get to Manchester from Boston.

Where to Stay in Manchester

• Kimpton Taconic Hotel: This mountain view hotel is a great weekend choice in Manchester. Take a leisurely soak in the huge bathtubs, relax by the pool or just enjoy the comfortable surroundings.
• Reluctant Panther Inn: This quirky named Inn also has an excellent onsite restaurant, as well as spacious rooms, beautiful wood furnishings, and fireplaces.

Saratoga Springs, New York

Saratoga is a quaint town in New York that is most famous for hosting the Saratoga Races!

These occur every summer, so if you’re lucky enough to be visiting during the summer months, then you’ll want to try to go and spend at least one day at the horse races.

It’s truly an unforgettable experience.

Other popular places in Saratoga to explore include Saratoga Spa State Park, Saratoga National Historical Park, and the National Museum of Dance & Hall of Fame.

There’s also a really gorgeous shopping area in downtown Saratoga, which is home to the Northshire Bookstore’s New York branch.

This bookstore is beautiful and it’s great to support local sellers.

How to Get to Saratoga from Boston

You’ll want to drive to Saratoga from Boston. You could also utilize the bus, but it will take a lot longer.

Where to Stay in Saratoga

• Batcheller Mansion Inn: As one of America’s great Victorian houses, built in 1873 and the site of many historical moments in Saratoga history, this is a stunning place to step back in time for your weekend trip. Beautifully preserved and steeped in history, well worth the trip!
• Saratoga Casino Hotel: For a more resort-style weekend trip this hotel is a perfect choice. Rooms are peaceful and huge, and there is a free shuttle service to take you into town to explore.

Portsmouth, New Hampshire

For a classic, small-town New England getaway complete with historic homes, a beautiful harbor, plenty of seafood restaurants, and a relaxed vibe, you can’t beat exploring the best things to do in Portsmouth, New Hampshire !

This gorgeous New Hampshire Seacoast is a New Englander favorite for good reason.

While you’re there, visit the popular Strawbery Banke Museum, shop the charming boutiques, explore downtown and the harbor on foot, and enjoy a seafood dinner on the water.

1 hour, 15 minutes.

How to Get to Portsmouth from Boston

You can reach Portsmouth from Boston by either bus or car.

Where to Stay in Portsmouth

• Ale House Inn: Located in a historic building that once housed a brewery, and with a complimentary bike hire this is a great choice for your weekend in Portsmouth.
• The Hotel Portsmouth: Located in Downtown Portsmouth this charming Victorian manor house has spacious rooms and is a short walk to all the amenities.

Acadia National Park, Maine

The first national park east of the Mississippi is absolutely one of the best weekend trips from Boston for those looking for some hikes, some stunning coastal views, and some of the best sunrises and sunsets in New England!

Some of the best things to do in Acadia National Park include watching the sunrise on Cadillac Mountain (during part of the year, this is the first place the sun rises on the continental USA!), strolling around Jordan Pond, hiking the Beehive Trail, checking out the Bass Harbor Headlight, and exploring the Carriage Roads.

Don’t forget to enjoy the charming things to do in Bar Harbor while you’re there, which is home to great restaurants, a cozy New England vibe, and plenty of beautiful places to stay!

4 hours, 30 minutes.

How to Get to Acadia NP from Boston

The best way to reach Acadia National Park from Boston is to drive. 

While there is a shuttle bus at the park in the summer, it’s vastly easier to visit Acadia with a vehicle.

Where to Stay in Acadia National Park

• Acadia Inn: Within 1 mile of the park and with its own nature trail that extends into the park this is the perfect spot to base yourself in Bay Harbor near the park.
• Bar Harbor Grand Hotel: Another great option in Bay Harbor is this palatial manor hotel with a swimming pool and hot tub.

North Adams/Berkshires, Massachusetts

The Berkshires is a beautiful region of western Massachusetts that is always highly overlooked and underrated.

This area is very rural land and is filled with lots of great outdoor activities.

This is also the perfect place to go if you are interested in seeing fall foliage near Boston that is (maybe) slightly less crowded than the White Mountains of New Hampshire.

North Adams serves as the perfect home base for exploring the Berkshires.

In North Adams, be sure to check out the Natural Bridge State Park, Windsor Lake, and Cascade Trail.

If it ends up raining a bit while you’re there, don’t worry, there are also lovely art museums and history museums worth exploring.

2 hours, 40 minutes

How to Get to North Adams from Boston

You can only get to North Adams from Boston by car, but you’ll pass some magnificent scenery along the way!

Where to Stay in North Adams

• Tourists: This incredible hotel is the perfect place to stay for your weekend trip. Designed like something out of an architecture magazine but still comfortable, warm, and welcoming.
• The Lodge: Another fabulous option set as private cabins with stunning decks to sit and enjoy the sunset.

Lake Champlain, Vermont

Lake Champlain is a gorgeous lake in Northern Vermont and Northeastern New York.

It’s absolutely beautiful and is filled with lots of great outdoor activities, like biking trails, hiking trails, kayaking, canoeing, swimming, and more.

The lake covers a lot of ground, so there are many great towns to set yourself in for exploring the area.

Of course, you could opt to stay in Burlington, but other popular areas to stay include St. Albans and Shelburne.

You could also choose to stay on the New York side, such as in Plattsburgh or Champlain.

Just know that the prices can drastically change depending on where you opt to stay !

4 hours, 35 minutes.

How to Get to Lake Champlain from Boston

Like most of the outdoorsy places, you do have to drive to get to Lake Champlain from Boston.

Where to Stay in Lake Champlain

• Green Mountain Suites: The perfect spot in Burlington for a classic cozy trip with open fireplaces, fluffy blankets, and an onsite hot tub.
• Back Inn Time: This aptly named hotel is perfect for a stay in St. Albans . Surrounded by pretty flower gardens, four covered porches, and two decks, relax in these comfortable surroundings during your weekend trip.

Kennebunkport, Maine

Kennebunkport is a beautiful town and coastal area in southern Maine.

The scenery here is absolutely breathtaking, from the Goat Island Lighthouse to Ocean Avenue.

Some popular places to explore here include Gooch’s Beach, Walkers Point, and the Rachel Carson National Wildlife Refuge.

There are lots of more secluded areas around Kennebunkport that you could easily stay in.

This makes it perfect for a quiet escape from the city, and ranks it among the best weekend getaways from Boston!

1 hour, 30 minutes.

How to Get to Kennebunkport from Boston

The only way to get to Kennebunkport from Boston is to drive, but you’ll drive right along the coast the entire time!

Where to Stay in Kennebunkport

• AWOL Kennebunkport: With cabin and suite options this is a perfect zen getaway in Kennebunkport. Enjoy the garden or the sun terrace between exploring the surrounding area.
• Waldo Emerson Inn: This classic New England inn is a great choice for your weekend trip. Relax by the fire or take advantage of the free bikes to explore the area.

About Kate Storm

In May 2016, I left my suburban life in the USA and became a full-time traveler. Since then, I have visited 50+ countries on 5 continents and lived in Portugal, developing a special love of traveling in Europe (especially Italy) along the way. Today, along with my husband Jeremy and dog Ranger, I’m working toward my eventual goal of splitting my life between Europe and the USA.

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Home | Travel guides | Road trips | Road trips USA | Top places to go on a road trip from Boston

• White Mountain National Forest
• Martha's Vineyard
• Berkshire County

Top places to go on a road trip from Boston

If you’re looking to get away from Boston for a bit, you won’t have to go far to find unforgettable experiences. Planning a road trip from Boston is easy given the variety of options available no matter what your interests are. You’ll find other cities, beaches, nature areas, and so much more. Here are the top 10 destinations for a road trip from Boston to consider.

1. Find fun in the sun at  Cape Cod

Driving time from Boston: 1 hour Distance from Boston: 70 miles

One of the best parts about taking a road trip from Boston to  Cape Cod  is how easy it is. This beachfront getaway is relatively close and offers numerous experiences you can’t find in Boston proper. You can hit the beaches and their rolling dunes, or you can relax with a round of golf on scenic courses.

2. Enjoy summer adventure in  Ocean City

Driving time from Boston: 7 hours Distance from Boston: 450 miles

Ocean City  on the Maryland coast is one of the best places to experience the Atlantic shore. Its 10 miles of beaches are remarkably well-maintained and suitable for the whole family. The waves are relatively mild, so the little ones can swim around safely. Be sure to stop by the boardwalk as well where you’ll find delicious seafood treats.

3. Trek through the trails at  White Mountain National Forest

Driving time from Boston: 2 hours Distance from Boston: 120 miles

At  White Mountain National Forest , you’ll find the answer to all your outdoor adventure needs. Just a short road trip from Boston, this area offers time away from the hustle and bustle of the city with hiking trails, stunning sights, and skiing opportunities across its 1,225 square miles. Be sure to keep an eye out for its diverse wildlife species as well.

4. Take the ferry to the island of  Nantucket

Driving time from Boston: 3.5 hours Distance from Boston: 100 miles

While  Nantucket  is technically an island off the coast of Massachusetts, you can still get there with a Boston road trip. All you have to do is hitch a ride on the ferry. Then, you can enjoy all Nantucket has to offer, with its humble stores with handmade crafts and extensive boating and fishing opportunities for the whole family.

5. Enjoy the weather at  Martha’s Vineyard

Driving time from Boston: 2 hours Distance from Boston: 90 miles

When your road trip from Boston takes you to  Martha’s Vineyard , you can enjoy one of the oldest summer travel destinations in the country. You’ll need to put your car on a ferry to make it all the way to the island, but in just 2 short hours or so, you can enjoy its warm weather and alluring beaches. Vineyards are especially popular in the area, so consider a tasting and a tour as well.

6. Explore the natural beauty of  Charleston

Driving time from Boston: 1.5 hours Distance from Boston: 90 miles

The small town of  Charleston , Rhode Island, offers a nice break from the vast metropolis that is Boston. Instead of towering skyscrapers, you’ll find a small town center with numerous salt ponds throughout. Because of the bodies of water around, you can enjoy all sorts of outdoor boating and fishing activities in addition to sandy beaches.

7. Visit the sailing capital of the world in  Newport

Rhode Island is home to numerous other islands including Aquidneck. That’s where you’ll find the city of  Newport . Its alluring coast has made it the sailing capital of the world where you can charter a boat and venture out into the water yourself. Of course, hiking through the green hills and playing the golf courses are available as well here.

8. Find lakeside fun in  Gilford

The main attraction in  Gilford , New Hampshire, is Lake Winnipesaukee. The town is settled along this lake and offers islands and beaches to explore. With a short road trip from Boston, you can see everything this town has to offer including a state forest, a ski resort, and an outdoor concert venue where you can watch live performances.

9. Explore outdoor fun in  Plymouth

Driving time from Boston: 1.5 hours Distance from Boston: 100 miles

The town of  Plymouth  in New Hampshire is known for bridging the Lakes Region and the White Mountains. With this kind of location, you can enjoy a wide variety of outdoor activities, whether you’re looking to scale a mountain or relax in a lake. Regardless of your interests, the whole family can find something to enjoy here, including beaches

10. Immerse yourself in culture in  Berkshire County

In western Massachusetts, you’ll find  Berkshire County . Easy enough to get to with a road trip from Boston, Berkshire is home to numerous cultural attractions that the whole family can enjoy, whether you’re interested in art, nature, or shopping. You’ll find refined art galleries and exciting, kid-friendly museums here like the Museum of Animation and Special Effects.

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37 Top Day Trips from Boston + Boston Weekend Getaways

There’s plenty to occupy your time in Boston proper, but the Massachusetts city is also a great base for day trips from Boston. We’ve been lucky enough to visit Boston and its surrounding towns several times, so we know how good the day trip scene can be.

There is SO much within a short drive of the city.

In fact, Boston’s proximity to all kinds of excursions within a few hours makes it one of the most bang-for-your-buck destinations in the United States.

Let’s dive into making the best Boston day trips happen and all of my favorites from my New England travels .

Disclosure: Please note that the post below contains affiliate links, including links through the Amazon Services LLC Associates Program. As an Amazon Associate, I earn from qualifying purchases .  At no additional cost to you, I earn a commission if you make a purchase. I won’t recommend something I have not used/would not use myself, and any income earned supports the upkeep of this site.

How many days in Boston is enough?

Three days in Boston is enough to see the main sights in the city, like The Freedom Trail, and tick off a Boston day trip.

With even more time in Boston, you can tackle more of these places to visit near Boston and short day trips from Boston.

Day Trips from Boston: Logistics

The assumption here is that you’re starting from Boston. If you’re not, you’ll need to get there, likely through Boston Logan International Airport.  There are all kinds of deals coming to/from that airport, so you’re sure to find something good no matter where you’re coming from, especially if you’re flexible with your travel.

You’ll also need a car to get to all of these fantastic places unless you’re sticking to trains and other public transportation. 

Where can I go without a car from Boston? The best day trips from Boston without a car are Providence, Rhode Island, and Salem, Massachusetts. Get to Providence on the South Station commuter rail, one of the best Boston day trips by train. Get to Salem on the North Station commuter rail. Both are quite walkable once you arrive, too.

You can also go whale watching on a guided excursion from Boston .

You’ll have more flexibility if you do a self-drive, though, and any day trips from Boston that I describe below were all accomplished by hitting the road in our own vehicle.

We were on a long road trip throughout New England for most of the day trips I’ll highlight here. If you’re not on as extensive a road trip as we were, book a car ahead of your arrival using an aggregator like Hotwire or Priceline .

Interested in a map of all the fun day trips from Boston and attractions I’ll highlight here? Follow the Google link below:

GIMME MY BOSTON DAY TRIPS MAP!

My top boston day trips.

All of the day trips I mention below in detail are trips I’ve taken. There aren’t any I’ve done that I wouldn’t recommend on a Boston day trip, so anything you’ll see here was a pleasant experience. I’m pretty easy to please, though, especially when there are lobster rolls available. Do with that what you will.

1. Salem, Massachusetts

Distance:  25 miles Drive Time:  45 minutes

At less than an hour’s drive, Salem’s spooky history was a no-brainer for our last trip to Boston. In fact, I’d call it the best day trip from Boston if you’re here in the fall. I highly recommend a visit in October when this New England town goes all in on its witchy history. I even put together a guide for you to make Boston day trips to Salem happen.

At the very least, visit the Salem Witch Museum for a recreation of the Salem witch trials. The impressive Peabody Essex Museum is also a must if you’re more into art galleries than all things spooktacular.

If you’re a movie buff, Salem also boasts quite a few filming locations for the original Hocus Pocus , a Halloween classic by any standard.

2. Plymouth, Massachusetts

Distance:  41 miles Drive Time:  1 hour

You have to see that big ol’ rock at least once in your life. Luckily, there’s more to do to fill up a day in Plymouth, an essential New England travel stop, outside of Plymouth Rock.

Gaze upon the 81-foot-tall National Monument to the Forefathers. Catch the views down below from Burial Hill. Stroll onto the Mayflower II for a round of Pilgrim cosplay. See the Plimoth Patuxet Museums, a complex that details life in the Plymouth Colony, including the indigenous experience.

Note: At one time these were called the Plimoth Plantation. The name was changed as a nod to the indigenous populations. It really wasn’t as hunky-dory as your childhood Thanksgiving plays might suggest, folks.

3. Hampton, New Hampshire

Distance:  51 miles Drive Time:  1 hour 5 minutes

We were in Hampton in the off-season, so it definitely was quite a bit sleepier than usual. In the summer months, this place comes alive as one of the best beach towns in the region.

If you visit in the fall as we did, expect sunsets like the one above, but not a ton in the way of open eateries and bars that cater to that summertime crowd. It’s still lovely and all kinds of peaceful if that’s what you’re after, though, especially when you realize it’s just a little over an hour drive from Boston.

4. Portsmouth, New Hampshire

Distance:  56 miles Drive Time:  1 hour 5 minutes

If you’re looking for fall day trips from Boston, this port town is a delight during the spooky season because that’s when all of the pumpkin people come out. If you want to know what the heck that’s all about, check out my guide to Portsmouth .

Don’t miss the Strawbery Banke Museum — yes, it’s really spelled that way — and Portsmouth’s impressive historical homes. Our favorite was the Warner House, one of the oldest brick structures in New England. Enjoy a taste of New England with popovers from the aptly named Popovers on the Square. Walk the bridge to the town of Kittery, Maine, on the other side.

5. Kittery, Maine

Distance:  59 miles Drive Time:  1 hour 10 minutes

Yes, you can walk from Portsmouth, New Hampshire, to Kittery, Maine. This part of town is called Badger’s Island, and if you keep walking north you’ll reach the non-island portion of this scenic town.

Explore the southernmost town in Maine with a visit to Fort Foster. The old military fortifications boast some historical significance, but the park is also home to three of the town’s beaches and a variety of trails.

If you’re not here to learn anything, trips to Kittery are also popular for shopping at The Kittery Outlets. That’s not my thing, but it may be yours.

If you’re still not here to learn anything but feeling thirsty, Tributary Brewing Company is a popular option among local beer fans. Nearby Woodland Farms Brewery has a variety of non-alcoholic options if you’re cutting back on the booze.

6. Providence, Rhode Island

Distance:  51 miles Drive Time:  1 hour 15 minutes

For whatever reason, Providence just isn’t as popular as other New England towns, even when it comes to peak fall foliage travel. That may be a bummer for Providence, but it’s good news for you. Paths less traveled typically mean more budget-friendly travel and fewer crowds. 

With one day in Providence, don’t miss the Rhode Island School of Design (RISD), Thayer Street on the Brown University campus, and the city’s plethora of historic homes.

Note: If you’re seeking hot deals, the Wrentham Village Premium Outlets in Wrentham, Massachusetts, are just a half-hour from Providence.

Not convinced yet? I have a post on all the reasons why Providence should be on your list for any travel to New England.

7. Cape Cod, Massachusetts

Distance:  70 miles+ Drive Time:  1 hour 40 minutes+

Is Cape Cod a day trip from Boston? Cape Cod can be a day trip from Boston, but the further up the cape you travel, the less time you’ll have for activities on the peninsula.

If you’re here for Provincetown and the Cape Cod National Seashore at the northern tip, expect that journey to take you closer to three hours. That’s likely too far for a day trip, so you may want to save the town’s Race Point Beach and the Mayflower landing site (also known as the Pilgrims’ First Landing Site on your maps) for a trip when you have more time.

If you really want to make a day trip to Cape Cod happen, I’d recommend Hyannis, instead. It’s home to one of the best bowls of chowder I’ve ever had at the Black Cat Tavern and the John F. Kennedy Hyannis Museum , but also that chowder.

Seriously, it’s the best.

Be aware that travel times to Cape Cod can also vary widely depending on when you visit. 

8. Newport, Rhode Island

Distance:  73 miles Drive Time:  1 hour 40

Newport, Rhode Island, is the perfect day trip to look at how the other half lives. I’m not really sure why that phrase is a thing, by the way, as us normal folk outnumber the “other half” by quite a bit. 

In any case, it’s known for its Gilded Age mansions. I have a Newport mansions guide if you’re interested.

If you’re not interested in Newport’s mansion scene, stroll the Newport Cliff Walk at the very least. You’ll still get mansions on the one side, but ocean panoramas await on the other.

9. Mystic, Connecticut

Distance:  100 miles Drive Time:  1 hour 55 minutes

I came to Mystic because of Mystic Pizza , but I stayed because it’s friggin’ adorable. If you just have the day, don’t miss my detailed guide to all things Mystic .

The pizza joint made famous by the movie is fine — I mean, you should definitely visit if you love Julia Roberts and just want to take in those vibes — but it’s even more fun to cruise around town and take in the seaport. Visit the Mystic Seaport Museum if you’re here for all things maritime. It’s the largest maritime museum in the country.

10. Portland, Maine

Distance:  112 miles Drive Time:  2 hours

Portland is the heart of Maine. It’s the state’s largest city with loads to do to fill up a full week. If you’re seeking day trips from Boston to Maine, this one should be at the top of your list.

If you only have the day, though, take the trip up to Portland Head Light on Cape Elizabeth and get another lighthouse fix at Bug Light. It’s not possible to get sick of these Maine lighthouses. I’ve tried! Get your arts fix at the Portland Museum of Art , the biggest and oldest art museum in the state.

If you’re here for that quintessential Portland beer, it has to come from Allagash Brewing Company . On a warm day, you can sit out on their large patio and enjoy the people-watching from folks being introduced to high-ABV beers.

Discuss when you’d like to return over a lobster roll from Portland Lobster Company . You WILL want to come back to this city. I’ve been plotting since I left.

11. Hartford, Connecticut

Distance:  117 miles Drive Time:  2 hours 20 minutes

Mark Twain fans will love a visit to the Mark Twain House & Museum . This was the actual home of Mark Twain (at that time known as Samuel Langhorne Clemens) and his family from 1874 to 1891. If you time things right, you can visit the Harriet Beecher Stowe Center , too. Unfortunately, it was closed during our own trip to Hartford.

As you’re in the capital of Connecticut, visit both The Connecticut State Capitol and Connecticut’s Old State House . The latter is now a history museum that offers up a primer on not only the state’s capitol building switch but a history of the state, as well.

12. New Haven, Connecticut

Distance:  139 miles Drive Time:  2 hours 25 minutes

New Haven is known for Yale University and all the impressive things that come with its connection to the Ivy League institution. That means it’s home to some of the best museums in the country and rare books libraries that you should really time your visit around. I have a guide to all of that and then some.

If you’re just on a pizza tour, I’ve got a guide for that, too. I even go so far as to name my personal favorite New Haven pizza. Have a look !

My opinions in that pizza post got me all kinds of attention, both positive and negative. Here’s the thing. I like what I like and you can like what you like, and we can all eat pizza in New Haven without limits. Xoxo, friends.

13. Woodstock, Vermont

Distance:  140 miles Drive Time:  2 hours 30 minutes

This is one of the best day trips Boston has to offer for its charm alone. Yes, Woodstock’s covered bridges really are that cute. My pup seemed to think so, too. Woodstock is one of the most popular stops on any leaf-peeping tour of New England for a reason. Well, maybe it’s a few reasons.

The covered bridges like the Middle Covered Bridge are certainly one, but the plentiful green spaces that turn bright colors of reds, golds, and oranges come fall is definitely another.

Downtown Woodstock is a great place to start thanks to The Green, the town’s central square and gathering place.

More Places to Go from Boston

I’ve been to Boston a few times, but I haven’t seen it all. Here are a few more ideas for where to go from Boston on your next trip to the Massachusetts city:

• Concord, Massachusetts (40 minutes): This one is just a 40-minute drive from Boston known for its American Revolutionary War sites. Get your culture on, too, with a visit to both the Ralph Waldo Emerson House and Walden Pond, the inspiration for impressive works from Henry David Thoreau. Finish off with the Old North Bridge. 
• Lexington, Massachusetts (45 minutes): If you’re already visiting Concord, you may as well visit its neighbor, Lexington, essentially a suburb of Boston. The town is home to the Lexington Common, also known as Battle Green. This is where the first shot of the American Revolutionary War was fired.
• Marblehead, Massachusetts (50 minutes): This seaside town is known for its historic buildings, lovely coastline, and connection to the U.S. Navy. The storied fishing town is often referred to as the birthplace of marine aviation and the Continental Navy, the military outfit that came before the U.S. Navy.
• Sturbridge, Massachusetts (1 hour 5 minutes): See the Old Sturbridge Village, a living history museum detailing New England life in the 18th and 19th centuries, or go on a hike at Wells State Park in this scenic Worcester County town. Sturbridge is known for bringing history to life through its historic attractions and frequent events.
• Newburyport, Massachusetts (1 hour 10 minutes): This coastal city near the New Hampshire border has an Old World charm made more obvious by its meaderies and historic port. In the summer months, it’s a popular beach day out destination for its proximity to Plum Island, an optional island tour, and the Parker River National Wildlife Refuge.
• Gloucester, Massachusetts (1 hour 15 minutes): Come to this coastal city for its fresh seafood. You can actually see fishermen (and women) working the waterfront here as you stroll the harbor. Gloucester is also known for its beaches in the summer months. Half Moon Beach and Long Beach are popular stops for relaxing and people-watching.
• Rockport, Massachusetts (1 hour 15 minutes): This seaside town near Gloucester is known for Halibut Point State Park and Halibut Point Reservation, recreational wonders that really come alive in the summer. While you’re there, don’t miss Motif Number 1, a replica of what’s considered the most-painted building in the United States.
• New Bedford, Massachusetts (1 hour 20 minutes): New Bedford is known for its history as a whaling port. If that strikes your fancy, don’t miss out on the New Bedford Whaling Museum , an immersive place that goes beyond the city’s maritime history and gives visitors a primer on whales and their habitats.
• East Bay Bike Path (1 hour 25 minutes): This 14.3-mile bike trail connects the Rhode Island towns of Bristol and Providence on one of the most popular trails of its kind in the region. Enjoy coastal views, eight different parks, and impressive waterfront mansions along the way.
• Ogunquit, Maine (1 hour 35 minutes): This coastal city is on the southern tip of Maine, making it an easy trip over the border from Massachusetts. Local museums, fresh produce, and a small local population that’s very welcoming to visitors make this a popular destination for anyone looking to slow things down a bit.
• Springfield, Massachusetts (1 hour 40 minutes): Springfield is a pilgrimage of sorts for any basketball fans out there, as it’s home to the Naismith Memorial Basketball Hall of Fame . The museum (and hall of fame) serves as a record not only of the history of the sports but the history of the biggest names in the game.

Best Weekend Trips from Boston

You’ll see quite a few of the weekend road trips from Boston below on posts detailing the best trips from Boston to do in a day. Personally, spending over three hours in the car one-way is a lot, especially if you’re traveling with a dog as we often are.

Here are a few trips that are best as Boston weekend getaways from my own experiences. 

25. Waterbury Village Historic Village, Vermont

Distance:  190 miles Drive Time:  3 hours 10 minutes

If you’re visiting Vermont in the fall months, you likely already have the Waterbury Village Historic District in your plans. If the weather holds up, you’ll also want to include a visit to Ben & Jerry’s in that Vermont itinerary.

Waterbury is the only place in the country where you can take a factory tour of the ice cream giant. At the very least, have a chuckle at the ice cream graveyard and mourn flavors that are no longer with us.

26. Stowe, Vermont

Distance:  199 miles Drive Time:  3 hours 10 minutes

Stowe is what all of your leaf-peeping dreams are made of. The colors in this place during those magical few weeks in autumn are more vibrant than anywhere else I’ve ever been. No matter when you visit, though, don’t miss out on The Alchemist Brewery, a brewery known for one of the best beers on the planet: Heady Topper.

Fun fact: I don’t even like IPAs but there was something about this one that hit just right. You have to drink it out of the can, too.

Interested in learning more about my favorite town in Vermont as you plan a trip from Boston to Stowe, VT? I have a guide to all of my favorite Stowe stops .

27. Montpelier, Vermont

Distance:  180 miles Drive Time:  3 hours 20 minutes

No, Burlington is not the capital city of Vermont. (I just have to put that out there as some of my peers failed to Google that one.) It’s Montpelier. You know I’m right because you’re looking at a pic I took of the Vermont State House above. That golden dome really is that vibrant, by the way.

If you’re traveling with a pup, don’t miss out on The Quirky Pet, a pet shop that’s home to several mops masquerading as dogs. You’ll know ’em when you see ’em.

28. Rockland, Maine

Distance:  189 miles Drive Time:  3 hours 25 minutes

Picturesque Rockland is one of my favorite towns in Maine. The lighthouse action alone here is worth the weekend trip from Boston. See the Rockland Breakwater Lighthouse and the nearby Owls Head Lighthouse and you’ll treat yourself to two of the most photogenic lighthouses in the state.

Owls Head and Owls Head State Park are technically just outside of Rockland, but it’s a 10-minute drive if you want to make it happen.

Rockland is also known for its lobster fishing industry, so if for whatever reason you’ve yet to eat a lobster roll, this is a legit place to do so.

29. Bangor, Maine

Distance:  240 miles Drive Time:  3 hours 25 minutes

We made the trip to Bangor for one reason and one reason only: the Stephen King house. Even though it’s no longer technically the Stephen King house — the author is now splitting his time between another home in Maine and a Florida home, for whatever reason — you’ll likely still find fans waiting out front.

Fun fact: On our visit in October, there was a red balloon tied to the spooky front gate in honor of that one clown he created. You know the one.

The folks who will be running the writer’s retreat at the property today will likely keep up the tradition for other tourists who want to visit the Victorian mansion. The place has wrought iron bats decorating the front gate, for Pete’s sake.

30. New York City

Distance:  215 miles Drive Time:  4 hours 10 minutes

New York City begs for as much time as you’re willing to give it. I could spend a full day just eating all of the quintessential New York foods and not even touch any of the cultural attractions. 

If you’re able, snag some tickets to a Broadway show while you’re there. You don’t have to drop the first and last month’s rent to make that happen, either.

Line up at the box office for same-day tickets if you’re of the patient sort, browse sites like TodayTix for rush tickets and day-of deals, or even take advantage of same-day resale tickets from desperate patrons of the arts. There are ways to make it happen, especially if you’re not trying to get in on the hottest ticket in town.

31. Acadia National Park, Maine

Distance:  280 miles Drive Time:  4 hours 30 minutes

Acadia is one the most beautiful national parks in the country, but it can be challenging to get to if you’re not already on the East Coast. If you have the time, make use of your proximity to Boston and visit Acadia.

Traveling with a pet? I have a guide for pet-friendly Acadia things to do .

Otherwise, don’t miss out on the park’s best hikes and sites, like the Ocean Path Trail, Cadillac Mountain, and Acadia’s unique carriage roads. This is a place that begs for more of your time.

32. Bar Harbor, Maine

Distance:  285 miles Drive Time:  4 hours 40 minutes

Bar Harbor is a natural base for travel into Acadia National Park but book well ahead of your trip if you’re visiting in the summer and fall months. The town is expensive thanks to that proximity.

Once you’re done at the park, there’s plenty to occupy your time in Bar Harbor proper. Walk the lovely Bar Harbor Shore Path, fish for Maine lobster, and visit Bar Island. Downtown Bar Harbor is worth your time, too. Charming Main Street is home to the town’s best restaurants and boutique shopping.

More Weekend Getaways from Boston

I’ve seen a lot, but there’s so much more to see! Check out some of the Boston weekend trips that top my list, including the fancy ones that just haven’t been in the budget just yet:

• Nantucket, Massachusetts (2 hours 30 minutes+): Some of these lists say you can do this trip in a day, but I really don’t recommend it. This is one of the Boston day trips by ferry, which is why I added that little + for emphasis. Your day trip could turn quite long if you miss the boat, and I mean that literally. Plan for a Nantucket weekend, instead.
• Stockbridge, Massachusetts (2 hours 35 minutes): Stockbridge is doable on a long day trip from Boston, but the Berkshires as a whole are really best experienced on a weekend away. That way, you’ll be able to indulge in the local food scene, take in a day hike or two, and spend some time exploring the region’s cultural pursuits.
• White Mountain National Forest (2 hours 40 minutes): The White Mountains span New Hampshire and Maine, although most of the best leaf peeping is supposedly in New Hampshire. While it’s doable from Boston if you’re feeling aggressive, from what I’ve heard, you’ll want to stay a while once you’re there, especially if you’re at all into hiking.
• Martha’s Vineyard, Massachusetts (3 hours+): Much like Nantucket, your travel time for Martha’s Vineyard will depend on ferries available on the day or weekend you take your trip. It’s much better to plan for a full weekend or overnight at minimum to get a feel for how the fancy set lives on this summer colony.
• Burlington, Vermont (4 hours 15 minutes): We traveled all over Vermont on our fall foliage road trip but never made it to the state’s largest city. It’s firmly at the top of our list for future Vermont travels for its scenery alone, nestled all cute in between the Adirondack Mountains and Lake Champlain.

Where to Stay in Boston

If you’re taking day trips from Boston, you’ll need somewhere to stay. We stayed outside of the city during our visit as we waited too late to book, but I wouldn’t recommend that. We spent more time sitting in traffic than it was worth.

Use the map below to plan better and book accommodations in Boston proper:

Why do people vacation in Boston?

People vacation in Boston because it’s a world-class city. It’s also a great base for day trips if you’d like to hit the road.

I’d love to return to Boston and tick off some of the one-day trips from Boston mentioned above that I haven’t gotten to yet. I’m telling you, this city is a fantastic base for adventures!

Ready for Short Day Trips from Boston?

Your Flight:  I use a variety of tools to find cheap airfare, but if you’re looking to book during a particular period of time, especially during busy times (e.g. autumn in New England), you should use  Skyscanner . Deals to Boston are fairly easy to come by, especially if you’re flexible with your travel.

For adventurous folks who travel on the reg, I also subscribe to  Going , formerly Scott’s Cheap Flights. You’ll get cheap flight deals from your home base straight to your inbox.

Your Accommodations:  I recommend  Booking.com  or  Hotels.com  as your main options for accommodations in Boston, or  Vrbo  if you’re seeking something Airbnb-like that isn’t that site. 

Hostelworld  is a great additional option for travelers on a budget.

Etc.:  For general travel goodies, visit my  Favorite Things  page. For more information on planning your travel, visit my  Travel Tools  page.

Inspired by these Boston day trips? Pin me!

Interested in more adventures within an easy drive? Check these out:

• You Have to Visit Vermont’s Dog Mountain
• Top Wineries at Cayuga Lake
• Explore the Best Breweries in Charlotte, NC
• Visit Virginia’s Natural Bridge State Park
• A Guide to the Best Stops Along the Blue Ridge Parkway

Ready to see more?

Subscribe to my biweekly newsletter for hot travel tips I come across, weird stories you won’t see elsewhere and perhaps lifelong friendship.

Too much, or just enough?

Agnes Groonwald

The Best Road Trips from Boston

Last Updated on October 9, 2023 by Kristin

Boston is a living American history lesson, boasting Revolutionary War landmarks like the Old North Church and Freedom Trail. With an endless array of incredible seafood restaurants and charming Irish pubs, it’s worth spending time in Boston to enjoy all the city has to offer. At the same time, New England’s biggest city is also a launch pad for a road trip to the numerous small towns dotting the Atlantic coast. Here are the best road trips from Boston.

Fabulous Road Trips from Boston

Note: Drive times are estimates, and can vary greatly due to New England traffic.

25 miles / 32 mins.

The quick jaunt northeast up I-93 and I-95 to Salem, Massachusetts may not seem like a proper road trip. However, this quaint city known for its witchcraft trials is a must-see attraction that quickly transports visitors to another world. Settled in 1626, the coastal city provides a mix of historical attractions like the Salem Witch Museum and a 171-foot replica of the Friendship merchant ship. Salem’s charming downtown is also home to an eclectic mix of specialty shops and cozy restaurants. >> Recommended hotels in Salem

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Newport, Rhode Island

84 miles  / 1 hr. 30 mins.

Head south from Boston on I-95 to reach Rhode Island, a tiny state packed with sprawling mansions, world-class museums and sandy beaches. The quaint coastal town of Newport is a popular summer haven known for its stately historic homes and breathtaking coastline. Stop by the Vanderbilt family’s summer home (called The Breakers) and drive down Ocean Avenue to enjoy one of the best spots in New England for sunsets. >> Recommended hotels in Newport

Portland, Maine

112 miles  / 1 hr. 45 mins.

Just a couple hours north up I-95 from Boston lies Portland, Maine, a charming port city known for craft breweries and lighthouses dotting Casco Bay. To catch an incredible sunset, drive about 15 minutes south to the Portland Head Light lighthouse in Fort Williams Park. One of the best things about a road trip to Portland is stopping at great beach towns along the way, including Ogunquit, Kennebunkport and Old Orchard Beach. >> Recommended hotels in Portland

116 miles  / 2 hr. 10 mins.

A trip to Cape Cod region from Boston is a must, especially in the summer months. To make the most of this road trip, cruise through the Cape’s historic towns, including Sandwich, Orleans and Wellfleet. The last stop on this route is the iconic Provincetown, known for its inclusive culture and LGBTQ+-friendly nightlife. Try to avoid driving from Boston to Cape Cod on Friday evenings in the summer, as this route becomes logjammed with heavy traffic as people leave the city for the weekend. >> Recommended hotels on Cape Cod

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White Mountain National Forest, New Hampshire

130 miles  / 2 hr. 20 mins.

For an outdoorsy road trip that takes you off the beaten path, set your sights on New Hampshire’s White Mountain National Forest via I-93. The forest spanning more than 750,000 acres is home to lakes, streams, hiking trails, ski areas and wildlife including moose, foxes and black bears. Accommodations range from campgrounds to luxury resorts with amenities like hot tubs and pools. One of the best scenic drives through the White Mountains is a 34.5-mile part of NH-112 known as the Kancamagus Highway (or “The Kanc”), which people flock to in the fall to watch the leaves change colors.

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8 Stellar Group Getaways from Boston In a Three-Hour Drive or Less

Did somebody say road trip.

Published on 10/12/2023 at 1:25 PM

Embarking on a road trip from Boston means two things: Escaping the hustle and bustle of city life and so many epic destinations to decide between within driving distance. Whether you're drawn to picturesque coastal hamlets, want to amble along a quaint main street, or are in need of some outdoorsy fun in mountain towns, New England has a road trip adventure for you and your crew. So, throw your luggage in the trunk and get ready for your next great escape from Beantown.

North Adams , MA

The magnificent Berkshires await. Get ready for cinematic vistas on the roughly two-hour-and-forty-five-minute drive from Boston to North Adams, MA. From Boston, head west to pick up the scenic and historic Mohawk Trail near Athol, Massachusetts, and follow it along to North Adams . New to the region? The Mohawk Trail Scenic Byway is a sublimely beautiful 69-mile drive passing through three Massachusetts counties complete with rolling hills, lush forest landscapes, Berkshire Mountain road climbs, farmlands aplenty, and Hallmark-worthy small-town roads. Once you’re in North Adams, you’ll journey along Hairpin Turn, one of the region’s most popular tourist destinations boasting panoramic views of the Hoosac Valley, Mount Greylock, and Mount Prospect.

During your time here, the posse should carve out at least a few hours to spend time at MASS MoCA , a contemporary visual and performing arts museum or for hiking around the Natural Bridge State Park (open May through mid-October), where you’ll see the only natural water-eroded bridge in America that is about 550 million years old. Meals in these parts are also worthy of hours-long blocks as farm-to-table dining invites lingering and learning from staff. Two great choices that promote this cooking M.O. in North Adams are The Break Room at events space Greylock Works , and Trail House , tucked directly off of the Mohawk Trail, with some of the best baked brie to meet your lips.

When it’s time to hit the hay, Hotel Downstreet has an indoor pool and hot tub for your group to enjoy. Plus, we like that they offer free coffee to-go from their local partner Tunnel City Coffee to keep everyone content (read: caffeinated). On your way to or from North Adams, road-trippers should also be sure to stop in Adams to see the Quaker Meeting House and Susan B Anthony Birthplace Museum ; the Bridge of Flowers in Shelburne Falls, a seasonal five arch foot bridge across the Deerfield River, built in 1908; and the Yankee Candle Company in Deerfield, Massachusetts (because there’s no such thing as too many fall-scented candles). It’s better in the Berkshires, indeed.

Gloucester , MA When traveling from Boston to Gloucester, hop out of the car for a walk along Singing Beach (named for the sand that “sings”) in the neighboring coastal town of Manchester-by-the-Sea. Now you’re officially in  The North Shore ! Gloucester , Massachusetts, located some 50 minutes from Boston is the craggy coastline town of your dreams, amplified by famous fishing heritage and several cultural institutions. Our vote is to visit Cape Ann Museum to satisfy both art and history buffs in your clique, followed by the Hammond Castle Museum , celebrated for its medieval and gothic architecture, or Maritime Gloucester , to school yourself on Gloucester’s working waterfront. Then, spend some time wandering about the Gloucester Harborwalk , and shuffle along to either Eastern Point Lighthouse or Annisquam Harbor Lighthouse (or both) for a group photo op.

In terms of lodging, the Beauport Hotel is worth the splurge for an oceanfront retreat you won’t soon forget (for travel brownie points, also take note that the property is located on the oldest fishing port in America). Seafood, of course, is the name of the dining game here and Seaport Grille , perched on the harbor with two decks offering ocean views and 1606 Restaurant and Oyster Bar , which has live entertainment on Tuesdays and Thursdays are two sure bets. As is Oliver’s Harbor Restaurant & Bar , a family-owned, contemporary American establishment where the mussels and sea scallops are divine.

Newport , RI

Some 72 miles from Boston (or a two-and-half hour drive) lies ever-winsome Newport. Come for the Gilded Age architecture, stay for the crab cakes, lobster rolls, and clambakes. To get acquainted with the terrain, take a scenic Newport Trolley Tour . Or, start your trip with Newport Mansion tours for a megadose of Gilded Age Splendor (FYI: Some mansions are only opened seasonally), and then stroll along the famous Cliff Walk for that rocky shoreline, Atlantic Ocean, and sprawling estate triple punch.

Speaking of that famed three-and-a-half-mile route, you’ll want to post up at The Chanler at Cliff Walk , where you and your friends will spend the happiest of hours on the property’s picturesque lawn that welcomes a wine garden in the summer, apple cider bar in the fall, and hot chocolate bar in the winter (whatever you sip on, make divvying up the costs of drinks a breeze with Zelle®). The hotel’s Cara restaurant doles out blind tasting menus that rotate daily for an unforgettable culinary experience, and nearby you can also feast at The Mooring Seafood Kitchen and Bar , Clarke Cooke House , and The White Horse Tavern . Visiting the International Tennis Hall of Fame is a must before you skip town.

Groton , MA

North Central Massachusetts at its finest can be found approximately 50 minutes from Boston in Groton, billed as “America’s original frontier.” On the way to Groton, get out of the car and stretch your legs in the town of Lexington, Massachusetts, as you check out the National Historic Landmark Lexington Battle Green and Minuteman Statue, a life-size bronze figure overlooking the battle green depicting a colonial farmer with a musket by Boston sculptor Henry H. Kitson. Also known as “Johnny Appleseed Country,” the great outdoors is a way of life in and around Groton. You’ll find rivers, lakes, forests, over 100 miles of trails, farmland, a plethora of wildlife, and a swath of protected open land space. Traveling with fellow hiking enthusiasts? There’s Groton Trails Network with 130 miles of maintained trails for you to tackle. Or swap sneaks for skimming on the Nashua River in West Groton with canoe, kayak, and SUP rentals through Nashoba Paddler . Another fun way to spend a day is hiking up to the historic Bancroft Castle, which dates back to 1906.

If you and your pals prefer diversions of the low-perspiration variety, sneak a peek at the concert lineup at Groton Hill Music Center or scope out the art exhibits at Goldring Piene Art Farm . For grub, allow us to point you towards Gibbet Hill Grill , an upmarket farm-to-table eatery or  Forge & Vine , where the restaurant’s pièce de résistance is an eight-foot wood-fired grill. The latter of which is the culinary hub of The Groton Inn , a boutique hotel on the town’s storybook main drag.

Waterville , ME

Yes, we know: Maine has a spectacular coastline. But take a turn from the coast to visit the city of Waterville, an up-and-coming New England arts and culture hub. Three hours from Boston, Waterville is already home to the respected Colby College Museum of Art , and the school recently unveiled the Paul J. Schupf Art Center on Main Street, which will also connect to the historic Waterville Opera House .

With this revitalization comes hotels you and your friends will actually want to plan a trip around, like the Lockwood Hotel , which, in 2022, became the first boutique hotel to open in the city in over a century. Inside the hotel, you’ll find the crave-worthy Front & Main , which has excellent dinner service and stellar Bloody Marys to pair with all the French toasts and eggs Benedicts your group will be ordering. Even if you slung back one too many bloodies, you’ll only have to walk across the street to Greene Block + Studios , an arts collaborative that hosts a rotating program of performances and exhibits, run by — you guessed it — Colby. Another day, fresh air fiends can rejoice in ample outdoor activities from hiking in nearby Pleasant Point Park or driving about 30 minutes to the Kennebec River Rail Trail for biking or a walk-and-talk en route to Boston.

Ogunquit , ME

For those who prefer a trip where you’re out and about, book your rooms at The Admiral's Inn , close to Ogunquit’s famous public footpath, the Marginal Way, and a beloved host for LGBTQ+ gatherings. Ogunquit in general is a popular LGBTQ+ destination, with many restaurants, galleries, and entertainment venues that are gay-owned and operated. Make yourself at home at Main Street , with dueling drag queens, holiday events, and more. The Front Porch , a cherished piano bar, is also worth swinging by on any Ogunquit itinerary. Or, buy tickets to catch a show at the Ogunquit Playhouse , with “Tootsie,” the Broadway musical currently playing and “The Sound of Music” on deck for the holidays.

Sometimes, you want a group getaway where you never leave the hotel. If that’s your objective, may we suggest Cliff House Maine ? It’s 77 miles or about a two-hour drive from Boston and has just about the best spa you’ve ever experienced. (Even the relaxation room with floor-to-ceiling glass windows overlooking the sea is a destination in and of itself.) After a massage and a manicure just plop down in an Adirondack chair on the lawn. From there, you can decide if you want to pop in the outdoor pool (seasonally) or indoor pool for a dip or curl up with your crew’s book club selection. Or how about screening a film in the theater or chipping away at a “crafternoon” with a craft class (like “Paint a Memory” lessons with the property’s artist-in-residence, Ric Della Bernarda)? Nestled atop Bald Head Cliff, eating is always a good idea at this luxe resort, too. We love having dinner by the fireplace at The Tiller or leaning into Maine’s lobster roll obsession at Nubb’s Lobster Shack . Before you close your tab (again, Zelle® to the rescue) get competitive with a few rounds of cornhole on the side lawn.

The one time you do head off-site, make the trek to Ogunquit’s seaside cliff walk, bustling downtown shopping area, and strip of sandy beaches open to the public year-round. And if you’re all about seeing lighthouses on vacation (who isn’t?) visit the Nubble Lighthouse in close-by York, Maine. If you need some inspiration for potential breaks during your drive, we’d recommend Portsmouth, New Hampshire. Grab java or tea at Cup of Joe Cafe & Bar on Market Street or grab a bite at the historic Gilley’s Diner , which can trace its origins back to a 1940 lunch cart. Black Trumpet , an inviting waterfront haunt from James Beard Award semi-finalist Chef Evan Mallet makes for a superb lunch stop, too.

Westerly , RI

Taylor Swift fans may know of Westerly: The singer has quite the sprawling mansion in the Watch Hill neighborhood. You can see said manse from the splendid Ocean House , which has plenty to keep the whole crew entertained like cooking and wine tasting classes in its Center for Wine and Culinary Arts, golf, croquet, and movie screenings in the on-property theater. And, oh yeah, there’s a heck of a spa and beach ripe for fishing, surfing, or lazing, too.

Or, check into the Weekapaug Inn , which has an in-house naturalist to take you out on Jeep safari tours, stargazing adventures, or hikes near the property. We’re also proponents of The Restaurant, which is heavy on coastal New England classics like oysters and lobster risotto or bisque, and The Bar, where cocktails are more creative than the venue’s name (make sure to end the night with a chocolate chip skillet cookie and vanilla ice cream). Both of these hotels are roughly two hours from Boston, and we’ll leave it to you and your loved ones to vote which snags your reservation. Either way, you’re in good hands and should check out Rhode Island’s capital city of Providence on either leg of your trip.

Wethersfield , CT

If your friend group moonlights as history professors (or, hey, that could be your real gig) we’re sending you straight to the small town of Wethersfield. Two hours from Beantown, you’ll arrive at Connecticut’s largest historic district with no shortage of enlightening experiences. Open seasonally, book it to the Webb-Deane- Stevens Museum which has a slew of exhibition galleries and access to an eight-acre campus and gardens — plus the option to take a guided tour of three restored historic houses. A walk down Main Street is equally rewarding; you’ll find shops like Old Wethersfield Country Store and Heirloom Market at Comstock Ferre and restaurants like Lucky Lou’s and The Charles . For those with a sweet tooth, good luck making it out of Main Street Creamery and Cafe with homemade regular ice cream, gluten-free options, lactose-free soft serve, and vegan ice creams without spending a Jackson. Come nightfall, relax with the bunch at Silas Robbins House , built in 1873 representing the Second Empire design with features like Victorian stenciling, moldings, draperies, and period furniture. What’s the only thing that could make this vacay better? Stopping at Ron-A-Roll Indoor Roller Skating Center on the way home to Boston.

Are you ready for a Road Trip? Explore these eleven incredible cross-country road trip routes across the U.S.!

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Atlantic Coast

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Southern Pacific

Home / Blog / Day Trips from Boston

Day Trips from Boston

Posted May 9, 2022 in Blog Posts

By Cameron Sperance, author of Moon 52 Things to Do in Boston Sometimes you just need an afternoon away to feel refreshed. If you’re looking for adventures close to home that you can fit into a single day, here are some day trips ideas that are all easy to get to from Boston.

Get transcendental at Walden Pond

Why go: Visiting Walden Pond is a perfect way to experience the great outdoors (and literary history) within minutes of some of the most congested streets of Boston and Cambridge. Where: The Walden Pond State Reservation is about a half-hour northwest of Boston and Cambridge, accessible via Route 2 from Cambridge and via Interstates 90 and 95 from Boston. The Massachusetts State Parks service offers the most up-to-date information on trails, parking, and hours of operation. Timing: The park is open year-round for walks, running, and hiking, but summer is the best time to visit if you want to swim or boat in the pond. If you do head up in the summer, be sure to arrive early—parking lots fill up quickly! Boat ramps are closed from early December through early April.

Roughly half an hour from Harvard Square is Walden Pond State Reservation, just outside the town of Concord. Made famous by the transcendentalist Henry David Thoreau who wrote Walden; or, Life in the Woods here in the 1850s, beautiful Walden Pond has become a favorite destination for Bostonians looking to de-stress and unwind while enjoying the simple beauty of nature.

Go beyond Harvard Yard in Cambridge and Somerville

Why go: Harvard and MIT are the two visitor magnets for Cambridge, a city separated from Boston by the Charles River. But these storied learning institutions have fueled a building boom in Cambridge and the neighboring city of Somerville, which have become lovely towns with exciting restaurant scenes and plenty of charm. Where: The easiest way to get to Cambridge and Somerville is on the MBTA’s Red Line subway. Most Cambridge destinations are within walking distance of three stops (Kendall, Central Square, and Harvard), while Somerville’s best hotspots are found near the Davis MBTA station. Timing: Autumn strolls around Cambridge and Somerville are the most scenic, with the changing leaves and the spectacle of the Head of the Charles Regatta. But winter is a good time to curl up in a cozy Harvard Square restaurant or Davis Square speakeasy. Spring can be rather hectic, especially during graduation season. Visit in summer to get sunny days without as many students.

Harvard Square and nearby Davis Square in Somerville (two stops north on the MBTA Red Line subway) have always been popular with college students, but they are also becoming more popular with the post-grad crowd. The growing food scene, fun nightlife, and an array of interesting shopping options surrounded by historic buildings all lend to the youthful energy here.

Get inspired at Mass MoCA

Why go: The Massachusetts Museum of Contemporary Art is a great, cultural motivation to head to western Massachusetts for a day or, even better, a weekend to explore the surrounding Berkshires region. Where: Mass MoCA is a little over two-and-a-half hours northwest of Boston on Route 2. The easiest way to get there is to drive. • 1040 Mass MoCA Way, North Adams, 413/662-2111 Timing: Fall is my favorite time to visit the museum, as it is also a perfect time to take in the colorful foliage in the Berkshires. But there is plenty to do year-round and particularly in non-winter months: Mass MoCA offers live events with dance and musical performances 40 weekends out of the year. You can spend at least an entire afternoon at the museum but incorporating it into a weekend trip is even better.

You may not expect one of the biggest forces of contemporary art in New England to be well beyond the confines of Boston’s urban core, but the Massachusetts Museum of Contemporary Art, also known as Mass MoCA, is just that: 26 restored, red-brick factory buildings in the Berkshires enclave of North Adams, packed with modern art.

Find quintessential New England in Newburyport

Why go: For the varied group torn between a beach getaway or finding a cute town in which to shop and dine, Newburyport has a little bit of everything for everyone. Where: Newburyport is a 45-minute drive north of Boston near the New Hampshire border on the Atlantic Ocean coast. It can also be reached in just over an hour on the commuter rail from Boston’s North Station. Timing: Newburyport and Plum Island can be enjoyed year-round.

There are oodles of cute seaside towns up and down the coast of New England—yet I find myself returning, at least once a year, to Newburyport and adjoining Plum Island. The mix of boutique shopping, cobblestoned streets, delectable restaurants, and seaside views in just a few blocks packs a lot into this coastal enclave. Nearby Plum Island is a barrier island and home to some of the more popular beaches where Newburyport locals go in the warmer months. The sandy dunes and expansive coastline make this a great spot for beach picnicking, sunbathing, and playing in the waves.

Go apple-picking

Why go: A fall apple-picking trek is a treasured New England pastime. Where: Carver Hill Orchard , 101 Brookside Ave., Stow, 978/897-6177 • Smolak Farms , 315 S Bradford St., North Andover, 978/682-6332 • Dowse Farms 30 Rockwood St., Sherborn, 508/653-2639 Timing: September and October are the best times to visit the orchards, but some, like Carver Hill Orchard, begin their picking season as early as July.

Apple-picking season is one of my favorite times to get just beyond the city and collect ingredients for some impressive farm-to-table pies. Lucky for me (and for you), there are several farms less than an hour outside Boston to satisfy fruit and cider cravings. No matter the farm, you’ll need to purchase their empty bags and containers, varying in size (typically $10-30), before venturing out into the orchards and farms for fresh produce. Fruit and veggie ripeness and availability are dependent on weather from year to year, so each year can bring an unexpected surprise, like late-season fruit, or an unpleasant disappointment, like fewer fruity options than you hoped. It’s never a bad idea to call ahead to see what’s in season and ready for picking!

Slurp oysters in Wellfleet

Why go: Nantucket, Martha’s Vineyard, and areas “down Cape” tend to get the heaviest summer crowds, as visitors flock to their beaches. Even Provincetown, at the very end of Cape Cod, gets packed due to its relatively easy access via the Provincetown Fast Ferry. But Wellfleet is known for more than just beaches. Its eponymous oyster is a mainstay in seafood restaurants, so head straight to the source to slurp down a dozen (or more) of these briny delicacies. Where: Bostonians reliably use the flexed arm as a Cape Cod map, and Wellfleet is about halfway up the forearm. It’s about a two-hour drive from downtown Boston. Timing: Wellfleet is a fairly easy day trip, especially if you’re planning on timing your visit around OysterFest in October. Leave Boston by mid-morning to arrive just in time for lunch. The late afternoon drive home can be longer, especially in peak summer months when traffic on Route 6 backs up from everyone leaving the Cape.

The Wellfleet Oyster is an integral part of any New England restaurant menu, as these smooth bivalves are a popular meal starter. Often overlooked by crowds passing through en route to Provincetown to the north, the fishing town of Wellfleet is the mecca of the authentic New England oyster experience. From beach shacks to fine dining, the Wellfleet Oyster’s namesake town offers many ways to enjoy a few of these salty gems of the sea.

Cruise Cape Cod on Old King’s Highway

Why go: The path that became Cape Cod’s Route 6A, or the Old King’s Highway, predates the founding of America and gives drivers a sense of what life on the Cape looked like before the rush of tourists, surf shops, and lobster shacks along the Cape’s more bustling roadways. Where: Route 6A runs 34 miles from the Sagamore Bridge in Bourne to the Orleans rotary. It banks north for the final 28 miles to Provincetown. Timing: If you don’t mind traffic, the peak summer travel season is the best time to visit due to the seasonality of some of the shops and restaurants along the way. But locals prefer the spring and fall shoulder seasons to avoid crowds.

While those clamoring to get to Provincetown on the Outer Cape as fast as possible might hop on the modern Route 6 to avoid stoplights, Route 6A (also known as the Old King’s Highway) provides a leisurely way to get a sense of the old Cape before it became a summer vacation hotspot. The highway starts in Bourne and meanders east through historic districts of quaint Cape Cod towns. It eventually banks north, and finally ends in Provincetown. The winding drive along scenic beaches, cranberry bogs, and town centers is a great alternative to the modernized highway of nearby Route 6.

Head East on the Mohawk Trail

Why go: Opened in late 1914, the Mohawk Trail is New England’s first official scenic route. The 63-mile stretch passes through 50,000 acres of Massachusetts state parks and forests, offering a variety of seasonal attractions for year-round enjoyment. Where: Start the Mohawk Trail near Taconic Trail State Park on the Massachusetts/New York border, a roughly three-hour drive northwest of Boston via Interstate 90 and Route 7. Timing: Take advantage of the chance to admire the natural beauty of fall foliage on your drive by cruising the Mohawk Trail in September and October.

Few things are better than loading the car up with tasty snacks, listening to a great playlist or audiobook, and cruising down the highway, enjoying beautiful views. In Massachusetts, a simple road trip is made even better when combined with cute towns, stunning landscapes, and famous historical landmarks. The Mohawk Trail, less romantically known as Route 2, offers the perfect 63-mile stretch through Massachusetts state parks and forests to make your scenic drive dreams come true.

Take in fall foliage

Why go: Driving to see fall foliage, or “leaf peeping,” brings millions of visitors each year to admire the vibrant changing colors of trees across much of New England. Why not see it for yourself? Where: Fall foliage can be observed anywhere in New England, from the trees of Boston Common to open fields in northern Vermont. But scenic drives in New Hampshire or Maine are some of the best and most popular options for taking in fall foliage. Timing: Leaves typically begin to change into their autumn coats of yellow, orange, and red in northern New England in September, while in areas farther south, the leaves turn a little later in the season. Most leaves have usually dropped by November, depending on when the first major frost or snow occurs.

Once you start to see the first hint of red or orange on a tree in New England, brace yourself: leaf peeping season has begun—and it’s serious business. The pumpkin spice lattes flow through the streets, plaid dancing troupes frolic through town, and apple cider donuts are the only thing you’ll find on local menus. Okay, I’m exaggerating—but not by much!

Plaid does tend to get a little more prevalent in the local sartorial spirit during these crisp months, and you will notice a significant spike in pumpkin-flavored anything on menus. This is also when many locals head to area farms for apple- and pumpkin-picking. And throngs of people take to the roads and head out of the city to Vermont, New Hampshire, and Maine to catch the first fall foliage of the season. If you want to join in (and you should; the foliage here can’t be beat), you have several options for a lovely scenic drive.

Shop local in Portsmouth, NH

It’s easy to pass up Portsmouth, New Hampshire, as a weekend getaway opportunity when compared to the bigger Portland, Maine, to the north or Providence, Rhode Island, to the south. But this charming seaside city offers a jam-packed day trip’s worth of shopping opportunities. It’s also fun to just stroll along the streets and admire the many window displays in the lovely boutiques.

Portsmouth is only an hour-long drive from Boston—on paper. I can’t stress enough that timing is everything here, as leaving basically anytime between 3pm and 6pm can turn this into a multi-hour voyage. Make a day of it and leave before breakfast to avoid traffic. Getting out of the city in the morning isn’t typically an issue, as most commuters are heading into the city.

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8 Amazing Day Trips from Boston To Try in 2024

Easy Driving Trips From Boston For a Great Family Day Out

When it comes to fascinating cities in the United States, Boston is always near the top of the list. It’s easy to see why, as there are endless interesting historical and cultural places to visit in Boston and the surrounding areas.

In fact, Boston has our vote as offering many of the best day trips in New England, most of which are less than two hours away! New Hampshire , Maine , and Rhode Island are all located conveniently close by, and you can reach all destinations by car or even public transportation.

Whether you’re interested in museums, sandy beaches, whale watching, or a spooky ghost tour, we have the adventure for you in our list of the best day trips from Boston.

8 Best Places to Visit Near Boston on a Day Trip

Salem, Massachusetts

Distance from Boston: 24.8 miles ~ via I-93 N and I-95 N (~33 minutes)

Salem is home to one of the most infamous events in America’s history – the Salem Witch Trials . And although this New England hamlet is particularly popular around Halloween, it’s one of the best places to visit near Boston year-round.

You can make the easy half-hour commute to Salem from Boston by car, train, or ferry. If you choose to take the commuter rail, Salem Station is on the Newbury/Rockport line . A one-way ticket is $8.00, and the commute takes about 30 minutes.

Have a little extra time? Take the scenic route by ferry from Long Wharf to Salem in the spring or summer. A one-way adult ticket costs just $25.

Salem was once a more important port than Boston and a prosperous hub of the China Trade. History buffs will enjoy experiencing colonial art and culture at the Peabody Essex Museum , one of the largest art museums in the region. We also highly recommend visiting the Witch Dungeon Museum , where visitors take a front-row seat at the Salem witch trials reenactments.

If searching for ghosts is more your style, sign up for the History & Hauntings of Salem Guided Walking Tour . Choose a nighttime tour by lanternlight and visit Burying Point Cemetery, Witch House, and Ropes Mansion garden while a local historian tells tales of Salem’s haunted history.

Top Tip: If you’re planning on visiting Salem in October, be prepared for crowds. We suggest purchasing tickets for tours, museums, and performances online ahead of time.

Salem, New Hampshire

Distance from Boston: 33.2 miles ~ via I-93 N (35 minutes)

Salem, New Hampshire, might not have the same haunting history as its Massachusetts counterpart, but there is still plenty to see and do in this small New England town.

This Boston day trip is only 35 minutes north of the city, so plan to spend the day shopping, exploring nature, and visiting America’s Stonehenge.

Yes, England isn’t the only place you can go to see mysterious stone structures! America’s Stonehenge is the oldest man-made construction in the United States.

Walking the half-mile trail through the ruins takes about an hour, so pack a good pair of hiking shoes! If you’re traveling with children, take them to the kids’ gemstone dig on site. They can keep up to three stones and get to use real archaeological tools!

Top Tip: The trail’s terrain can be rough and rocky, so if you’re traveling with a baby, choose a backpack carrier over a stroller.

Continue your outdoor adventure by visiting Canobie Lake Park , a full-sized amusement park the whole family can enjoy. There are rides for every age, including the Yankee Cannonball, the Canobie Corkscrew, and the Untamed. Younger children can enjoy a carousel, the Caterpillar, and several water rides. 

If you need some retail therapy, head over to the Mall at Rockingham Park. New Hampshire doesn’t have sales tax, which means you have more to spend at popular name-brand stores like Macy’s, American Eagle, and Michael Kors. You can also take in a movie at Cinemark Century Theatres or grab a bite to eat at one of over 15 food outlets.

• Continue your exploration of New Hampshire with these exciting scenic drives

Stow, Massachusetts

Distance from Boston: 29.2 miles ~ via MA-2 W (43 minutes)

If you’re searching for one of the best scenic drives from Boston in the fall , Stow is the place for you. The area offers many brilliant views of autumn foliage, and a 45-minute drive will transport you from the bustling city to the peaceful countryside.

Honey Pot Hill Orchards is one of Stow’s largest attractions for families, and it’s a great place to spend an afternoon picking apples, snacking on delicious cider donuts from the farm store, and visiting the animals.

View this post on Instagram A post shared by Honey Pot Hill Orchards (@honeypothillfarm)

You can also visit Carver Hill Orchard, Derby Ridge Farm, and Shelburne Farms. Each one has something different to offer.

You can also visit the American Heritage Museum , which has an extensive collection of antique planes, cars, and World War II tanks. It takes roughly two hours to take in the entire museum experience, so plan your time accordingly. Children will love the immersive exhibits, and you can even see a Revolutionary War Re-enactment during the museum’s Summer Living History Weekends. How exciting!

Before heading home, satisfy your hunger with a plate of mouthwatering authentic Italian fare at Trattoria Amalfi at the Nettle’s Plaza. Both of the restaurant’s owners were born and raised in Italy, and they’ve created a Mediterranean paradise in the heart of Stow.

Providence, Rhode Island

Distance from Boston: 50.9 miles ~ via I-93 S and I-95 S (54 minutes)

Less than an hour from Boston, Providence perfectly combines small-town charm and big-city culture. Whether you’re searching for things to do outside of Boston with family or friends, you won’t be disappointed with everything Providence offers.

Enjoy an authentic Venetian experience, New England-style, by going on a gondola ride along the Providence Riverwalk. Providence’s gondolas are believed to be the first authentic Venetian gondolas ever built on American soil, and they’re a sight to behold.

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Are you looking for additional sightseeing opportunities on the water? Then you must check out WaterFire , a series of almost 100 bonfires spread out over Providence’s three rivers.

Many great family activities are available in Providence, like Roger Williams Park Zoo and the Providence Children’s Museum. The zoo is the nation’s third-oldest and home to elephants, red pandas, snow leopards, a Komodo dragon, and many other fascinating creatures.

The children’s museum is Rhode Island’s only hands-on museum for kids, and all of the exhibits encourage active play and exploration.

• You may also want to check out this selection of scenic drives and byways in Rhode Island to extend your trip to Providence

Plimoth Plantation, Plymouth, Massachusetts

Distance from Boston: 40.5 miles ~ via I-93 S and MA-3 S (54 minutes)

What if we told you that an hour’s drive could transport you back in time to the 17th century? Well, it’s almost true! Plimoth Plantation is one of the best day trips in Massachusetts because you can spend an entire day totally immersed in America’s history.

Visit Historic Patuxet to learn more about Wampanoag communities and their way of life in the 17th century. You can visit a wetu (house), observe staff building a canoe, and more. Modern interpreters guide you through the site and provide fascinating insight, and you can usually experience Patuxet in about an hour.

Experience a typical day in the life of a Plymouth Colonist when you visit the 17th-Century English Village. Explore timber-framed houses, gardens, and spend time chatting with inhabitants of the colony. Learn about 17th-century defense by participating in a muster drill, playing Pilgrim games, and even trying your hand at pounding corn! 

Top Tip: Since Plimoth Patuxet and Plimoth Grist Mill are about three miles apart, it’s wise to drive the distance instead of walking. It’s wise to wear comfortable clothes and tennis shoes, as you will be walking a great deal.

• Extend your journey further with these 5 historic scenic drives in Massachusetts

Portsmouth, New Hampshire

Distance from Boston: 61.6 miles ~ via I-95 N (59 minutes)

Portsmouth is located just an hour north of Boston and is one of our favorite Massachusetts day trips. It’s filled to the brim with unique shops, historical locations, and delicious restaurants, making it an excellent option for the whole family.

Portsmouth beaches are a cut above the rest, having been ranked in the top five cleanest beaches in the country. Build sandcastles, stroll along the shore, splash in the waves, or soak up the sun. There are many beautiful beaches and parks to explore.

Take in Portsmouth’s historic culture and contemporary visual arts scene with a professional theater show or a trip to the Museum of New Art . Then, immerse yourself in the town’s history with a visit to the Strawbery Banke Museum , a 10-acre outdoor history museum that’s truly a sight to behold.

Knowledgeable staff in historical clothing are happy to talk with you about Portsmouth’s history and daily life in those early days. We’re positive you’ll be hungry after all that walking, so grab a slice at Flatbread Pizza before continuing on.

Cape Cod, Massachusetts

Distance from Boston: 70 miles ~ via MA-3 S (1 hr 14 minutes)

If you want a truly memorable day trip from Boston, there’s nothing more “New England” than Cape Cod . Cape Cod has it all, from miles of pristine white shoreline to kid-friendly amusement parks, making it one of the most popular vacation destinations on the east coast .

There are many opportunities to get out and enjoy nature in and around Cape Cod, like the Cape Cod Trail. Bike, hike, rollerblade, or even horseback ride this picturesque pathway around six towns and marvel at the area’s natural wonders.

Heritage Museums and Gardens is also a fantastic family destination in Cape Cod , where your children can play at Hidden Hollow, one of New England’s top play areas for kids. And don’t forget the Zip Lines and Climbing Fun for both kids and adults!

And, of course, no trip to Cape Cod would be complete without visiting Whydah Pirate Museum in West Yarmouth, home to the only pirate treasure in the world. Kids can climb aboard a replicated galley of the Whydah, see thousands of fascinating pirate artifacts, and search for missing pirate booty.

Top Tip : The best times to drive to Cape Code are Sunday through Thursday. If you’re traveling there on a Friday, try to arrive before 2 p.m. If you’re planning a day trip from Boston on a Saturday, arriving before 8 a.m. or after 2 p.m. is best to avoid the traffic.

Mystic, Connecticut

Distance from Boston: 99.5 miles ~ via I-95 S (1 hr 37 minutes)

Mystic might be our list’s longest day trip from Boston, but it’s well worth the journey! This picturesque Connecticut seaside village was once a thriving shipbuilding port. Today it’s a popular tourist destination for anyone who wants to get off the beaten path and enjoy some small-town New England charm.

Mystic has many diverse shopping opportunities, so take a stroll downtown and visit Mystic Knotwork, where they hand-tie bracelets, wreaths, and much more. Grab a Mystic t-shirt from Tidal River Clothing Co. as a souvenir and experience many other unique boutiques and eateries in the Mystic Bridge Historic District.

Spend a morning or afternoon at the Mystic Seaport Museum , the nation’s leading maritime museum. Here, you can visit Mystic’s recreated seaside village and meet all types of historical figures, from blacksmiths to shipwrights. You and your kids can even board the Charles W. Morgan , the last wooden whaleship in the world. There’s so much to see and do year-round in Mystic!

• Continue your road trip through Connecticut with these beautiful scenic drives

More Road Trip Ideas From Boston

If you’re looking to extend your journey from Boston even further, you may want to check out next:

• Road Trip Boston to Bar Harbor – a fabulous journey through coastal Maine, taking you to the most treasured national park on the East Coast.
• Or head northeast on this incredible Boston to Toronto road trip , taking in the highlights of Upstate New York and, of course, Niagara Falls.
• Don’t miss our favorite 5-day fall road trip through New England to capture the best autumn colors and experiences, or choose from one of these four incredible road trips through New England in the fall for a perfect weekend getaway.

© Family Road Trip

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Where to go in Maine? Looking ahead to summer 2025! - Maine Forum

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Where to go in Maine? Looking ahead to summer 2025!

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Maine is so huge that I would love some help narrowing down the options. Would be myself, my husband, and our 3 girls who will be 10, 13, and 16. We are most interested in unique nature experiences (marine wildlife, moose, mountain views, etc), tide pooling, rocky coast, moderate and scenic hikes (max 6-8 miles, maybe a bit less if a lot of elevation changes). Also interested in history/local culture and trying some local food (lobster, clam chowder?, blueberry things). We are not so interested in sandy beaches or general Northwoods types of things because we have that closer to home in the Great Lakes region--would prefer to focus on things unique to Maine/New England.

We do not enjoy crowds/traffic, black flies/mosquitos, or having to pick up and move every night--prefer to stay someplace at least 2-3 nights. We enjoy camping (both for budget reasons and because we find it helps with our crowd strategy) but have generally broken it up on longer trips--4 nights tent camping, 3 nights cabin/hotel, 3 more nights camping, etc. We probably have a max of 10-12 days to play with, after taking out travel days to/from Wisconsin.

I was looking at the northern Maine coast around Cobscook Bay State Park, also Moosehead lake area (would love to hike Gulf Hagas), Baxter State Park , Acadia NP. Not sure if Acadia is worth fighting the summer crowds or if some similar experiences can be had combining less crowded areas? We have visited & very much enjoyed other crowded parks (Smokies, Rocky Mountain, Glacier, Yellowstone) and just avoided the worst of the crowds by getting up early and resting in campgrounds or picnic areas mid-day when there is most traffic. Kennebunkport and Boothbay also had boat tours that looked interesting (would love to see puffins, seals, whales, and/or lobster trapping, etc), but they are a bit of a hike from the other areas I was looking at. We are used to bringing a lot of food along so don't need constant access to restaurants or civilization.

Any suggestions from people who are familiar with the areas to help me narrow things down would be so amazing! Thanks!

6 replies to this topic

Do include Acadia and have at least 3-4 nights there. It's worth it. You have it right...go early or late. You'll avoid lots of crowds that way.

We enjoyed Greenville at Moosehead Lake . We day tripped to Baxter State Park . Stay closer to Millinocket if you want to spend any time inside BSP.

We stay in a town called Southwest Harbor on the “quiet side” of Mt Desert Island. We head over to Bar Harbor and into the park when we want and enjoy the quiet of SW Harbor when we’re not touring the island. There are grocery stores and some restaurants so you’ll have the option of eating out or in (same for Bar Harbor - a larger grocery store there and many, many wonderful restaurants and little shops).

There is definitely camping available on the island. We rent through either VRBO or one of the real estate companies there (Knowles is our current favorite). In high season, rents usually go by the week so that may not work for the amount of time you have. There are yurts there, if that might work:

https://www.acadiayurts.com/

Your strategy of getting up early and heading to the park will work well. That is what is recommended in the busy summer months….

Check out this webpage for a lot of information about sites to see and hikes to take:

https://acadiamagic.com/

There are a number of boats that you can take out into the water - whale watches, lighthouse tours and puffin cruises . Here is info about a company that does puffin tours:

https://www.barharborwhales.com/lighthouse- cruises /puffin-lighthouse- cruise /#:~:text=Binoculars%20and%2For%20a%20long,taken%20with%20a%20zoom%20lens.

Sorry about that link - let’s see if this is better:

https://www.barharborwhales.com/lighthouse-cruises/puffin-lighthouse-cruise/

We enjoy the Acadian Nature Cruise but we're contemplating doing a different one when we visit in August. We'll also be there in 3 weeks. lol We're addicted.

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Professor who super-commutes from li to boston explains why it’s less stressful than going into nyc daily.

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She’s trained for this commute.

A professor who has super-commuted from Long Island to Boston for the past 10 years says she prefers the lengthy roundtrip Amtrak ride each week over the daily grind of going into New York City.

Suffolk County resident Leora Lanz, who teaches at Boston University where she’s also an assistant dean, insisted her 10 hours on an Amtrak train between the Big Apple and Beantown has been rewarding — as she broke down for The Post how she and her family have pulled off the feat since January 2015.

The married mother of three said when she’s shipping up to Boston, she gets on a Long Island Rail Road train on a Monday morning that gets her into Penn Station in an hour and then she boards an Amtrak Acela for the roughly four-hour ride.

By Thursday or Friday, she’s on another Amtrak back home. The cost for a roundtrip ticket is usually between $150 and $200 because she books several months in advance.

When Lanz used to go into the Big Apple every day for work in the hospitality field, between LIRR rides and bustling subways, it ate up a similar amount of commuting time over five days.

But the trips to the New England city have actually improved her quality of life.

“It’s funny because a lot of folks would be like, ‘Wait did you just say you work in Boston? That’s crazy,’” she said. “And I would say no, I think it’s nuts to go back and forth to Manhattan every day because I’ve done that for 10 years, too.”

Lanz said she’s more productive on the train to Boston, whether it’s grading papers, returning emails or preparing for classes at BU’s School of Hospitality Administration. She also treasures the downtime aboard Amtrak by watching movies, reading books and taking in the serenity of the Connecticut coastline.

Her one complaint: she wishes there was better Wi-Fi on the trains.

When she was first offered the job, her three children were 17, 15 and 10. It was supposed to only be for a semester, but the family impressively figured out how to make it work for a much longer time.

She and her husband would get a week’s worth of school lunches and snacks ready on Sunday before she left for Boston the next day.

She acknowledged her kids also had to become more self-sufficient and credits other family and friends for helping her achieve a job she loves.

Technology, including Skype, Zoom and FaceTime depending on the year, also helped keep the family connected.

“I love having my profession, something that’s mine, and by the time I come home at the end of the week, we’re really happy to see each other so it’s kind of nice,” she said, noting it’s easier with her three kids grown and on their own.

Before COVID-19, while Lanz still took the train to Boston, she flew home into JFK International Airport.

Lanz used to rent Airbnbs when she first started, but now has a friend in the hospitality field who helps her with housing.

Lanz is on sabbatical this semester, but is gearing up for fall in a position that gives her purpose even if the costs of traveling and stays can add up.

She was inspired to take the Boston University job because an old professor from Cornell University, where she went to college, had a lasting impact on her and was also a “super-commuter.” He would zip between Florida and upstate New York.

“If he did Orlando to Ithaca, I can easily do Long Island to Boston,” she quipped. 

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• Boston Red Sox

Red Sox Flex Home Run Muscles To Start Off Road Trip Opener

Watch these homers go.

The Boston Red Sox needed an offensive spark after a disappointing 3-7 homestand.

Boston arrived in Pittsburgh to start a road trip without two big bats in the middle of the order against the Pirates. They’d need other capable hitters to step up. Luckily for the Red Sox, Wilyer Abreu and Triston Casas answered the call.

Abreu showed better swings in recent games and wasted no time launching his first home run of 2024 in the first inning that nearly landed in the water behind PNC Park.

Wilyer Abreu's first of the season! 💪 #RedSox pic.twitter.com/HpVxb0PGtE — NESN (@NESN) April 19, 2024

Two batters later, Triston Casas stayed hot for the Red Sox, slapping a solo shot the other way to double the lead. Boston’s first baseman needs to keep the power supply coming for the ballclub. He’s done just that, now tallying four home runs in his last eight games.

Story continues below advertisement

1 wasn't enough in the inning 😤 #RedSox pic.twitter.com/NYNlcdWpQp     What do you think?  Leave a comment. — NESN (@NESN) April 19, 2024

Later in the fifth inning, Rob Refsnyder joined in on the fun , blasting his first home run of the season to the opposite field as well for Boston.

Welcome back, Rob Refsnyder! 🙌 #RedSox pic.twitter.com/wWPZFmquVi — NESN (@NESN) April 20, 2024

Ceddanne Rafaela felt ready for his first 2024 homer , doing so one inning later.

Rafaela's first of the season, and the Sox's 4️⃣th of the game! 🔥 #RedSox pic.twitter.com/XTV0aLdp9H — NESN (@NESN) April 20, 2024

Boston visits Pittsburgh for just the third time since the 2014 season where the Pirates earned a sweep. The visitors returned in 2022 when the Red Sox responded with a series win.

The Red Sox search for a win in Pittsburgh to start the road trip on a high note before travelling to Cleveland next week. You can catch the game on NESN .

About the Author

Tim Crowley

Digital Content Producer

The other "TC" at NESN. Hofstra Alum. The history buff of random baseball players of the 2010s.

In This Article

• Triston Casas
• Wilyer Abreu

Featured image via Charles LeClaire/USA TODAY Sports Images

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