10 Most Popular Day Trips from Boston, Massachusetts

Planning the perfect trip to Massachusetts? Save some time to explore some of the best day trips from Boston, MA. Within a few hours’ drive from New England’s largest city, travelers can experience historic towns, beautiful beaches, and tourist attractions that’ll create unforgettable memories.

Travelers looking to escape the hustle and bustle of Boston for a day or two will be delighted to adventure through New England. Visit historic villages and seaside towns around Cape Cod, and immerse yourself in natural beauty at outdoor gems like Halibut Point State Park while crossing several New England states off their list during your side trips.

Have some extra time to explore on your trip to Bean Town? Venture outside the city limits to experience New England’s magic with this guide to the top-rated Boston side trips.

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Cape Cod, MA

Cape Cod is the quintessential New England beach experience. Located to the Southeast of Boston, the long crescent-shaped stretch of beautiful beaches are lovely places to escape the city, soak up the sun, and take a dip in the Atlantic Ocean. A road trip from Boston to Cape Cod takes under two hours, making it the perfect day trip.

Cape Cod, Massachusetts

Travelers who enjoy history will love exploring the villages of Cape Cod, like Provincetown, the site of the Mayflower’s landing in 1620. Every type of traveler can find something fun to do in Cape Cod.

Nature lovers can explore parks like Monomoy National Wildlife Refuge. There are also plenty of world-class museums specializing in everything from classic cars to fine art.

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Venture to traditional lighthouses on the coast or hop on a ferry to the gorgeous resort towns of Martha’s Vineyard. Wrap up the day with delicious seafood before heading back to Boston.

Newport, RI

Head to Newport, Rhode Island, and take in the luxurious Gilded Age mansions of New York City’s elite. Once the summer playground of the mega-wealthy tycoons, Newport remains a gorgeous destination year-round.

The Breakers

The elaborate houses in Newport demonstrate the finest 19th- and 20th-century architecture in New England. Historic preservationists have restored many of the palace-like homes to their original glory.

Visitors can tour many of the properties and imagine what it might have been like for the mega-wealthy who once lived in the monstrous homes.

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The Breakers—a glitzy Italian Renaissance-style mansion with 70 rooms and a three-story dining room—will make visitors feel as though they have stepped back in time. Marble House is also worth a visit with its gorgeous salon and luxurious Chinese Tea House.

After touring the historic mansions, travelers can take a hike along the iconic Cliff Walk path to see them from the shore.

Concord, MA

History buffs will rejoice on a visit to Concord, MA, the location of the first battle during the American Revolution. Just outside of Boston, the town of Concord is rich in military history and beautiful architecture.

Walden Pond

In addition to the Revolutionary War history, many brilliant 19th-century minds once called Concord home. Ralph Waldo Emerson, Henry David Thoreau, and Louisa May Alcott are just a few famed thinkers and writers who lived and worked in Concord during the transcendentalist period of American Literature. Visitors can experience the places that inspired them as they tour their homes, like Alcott’s Orchard House.

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You can even visit the famous Walden Pond, a natural retreat where Thoreau built a cabin and lived while contemplating the meaning of life, spirituality, and nature. Walden Pond is a magical place full of natural beauty and worth a day trip all on its own. Walking in the footsteps of some of America’s most brilliant and creative minds might inspire you too!

Lexington, MA

On April 19, 1775, the sound of gunfire echoed from what is now the Lexington Green, also known as Battle Green. Those shots would mark the start of America’s War for Independence and forever cemented Lexington, MA, in American history.


An ideal day trip for history buffs and American Revolution enthusiasts, Lexington is located only 25 minutes from the city of Boston. It’s an excellent option for a full or half-day trip. Ambitious day-trippers can combine a trip to both Lexington and Concord for a full day of historic fun.

Gorgeous parks, sculptures, and historical attractions are just a few elements that make the beautiful town of Lexington well worth a side trip during your Boston vacation. Viewing historical reenactments is a popular activity for tourists. Many locals participate in the performances as a way to remember the American soldiers who helped to win America’s independence.

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You can even visit the immaculately restored 1710 Buckman Tavern, where the militia used to come together to strategies. Or walk through Minute Man National Historic Park to immerse yourself in Revolutionary War History.

Rockport, MA

Travelers looking for a seaside retreat with plenty of nature without venturing too far from Boston should head to Rockport, MA. Located only an hour outside of Boston, Rockport, Massachusetts, is an idyllic seaside town that makes for an excellent day trip. Explore the rocky landscape of Cape Ann on a rigorous hike or relax and enjoy nature at Halibut Point State Park.


Visitors can try their hand at recreational activities such as swimming, sailing, diving, or kayaking. Rockport makes the perfect side trip from Boston with rugged cliffs and a beautiful village for nature lovers and outdoor enthusiasts. Local outdoor outfitters offer stand-up paddleboarding tours, seal tours, and island tours.

Even with all of the exciting activities, you might just choose to spend the whole day relaxing on the pristine beaches and enjoying a picnic lunch. If you’re visiting on a Saturday, don’t miss a trip to the Rockport Farmers Market, which is open in the morning until noon. It’s the perfect place to find tasty local delicacies to pack in your picnic basket.

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In addition to plenty of nature time, Rockport has a pretty downtown area and plenty of romantic dining options for couples to enjoy during their vacation. Drink wine at a waterfront restaurant and gaze out over the ocean to wrap up an unforgettable day trip!

Newburyport, MA

Fancy yourself a historic architecture enthusiast? Head to the coastal town of Newburyport, MA, for an incredible day trip. Only 35 minutes from Boston, the city of Newburyport has ten historic neighborhoods for travelers to enjoy.


The entire downtown area is full of well-preserved historical buildings. Explore Newbury Historic District and wander the streets admiring the architecture or enjoy a show at one of the many performance venues before returning to Boston.

Travelers who enjoy getting outside in nature will love walking along the boardwalks through the sand dunes and the woodland paths along the beach at Parker National Wildlife Refuge.

From the coast of Newburyport, you might even catch sight of the mysterious Plum Island in the distance, which was used as an infectious disease research facility for years. Although the government-controlled island remains closed to the public, they plan to put it up for auction in 2022.

Portsmouth, NH

Portsmouth, New Hampshire, is an excellent choice for a day trip from Boston for those who like museums, breweries, and historic homes. It’s the oldest city in New Hampshire, dating all the way back to 1623. The historic town is full of attractive 17th- and 18th-century buildings and includes several historic homes that visitors can tour.


An abundance of cultural experiences await travelers in Portsmouth. Live theater performances, arts festivals, and a lively bar and restaurant scene are just a few of the exciting experiences visitors can enjoy.

Green spaces are abundant, especially within Prescott Park, a 10-acre public park with gorgeous colors from spring until fall.

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Visiting during the warmer months? Prescott Park hosts a variety of fun outdoor concerts and events and arts festivals. Free park tours at 11:00 AM and 1:00 PM on Fridays during the summer begin at the Liberty Pole.

Providence, RI

Art lovers and creative types will find a vibrant community in Providence, RI. Rhode Island’s largest city is just a little over an hour from Boston; it’s a fun side-trip that allows travelers to explore more of New England’s cultural highlights.


Providence’s hip downtown area is a great stomping ground for travelers who like to keep it trendy. Plenty of murals offer ample opportunities to snap the perfect photo to brighten up your Instagram feed.

Fun things to do in Providence, RI, include visiting art museums, hiking, and shopping. Architecture lovers will appreciate the city’s unique buildings in Art Deco and Victorian styles.

Those who love shopping can’t miss visiting The Arcade, America’s first shopping mall, which has been around since 1828. Shop until you drop at one of the world’s oldest malls.

Of course, no visit to Providence is complete without eating and drinking at the many tasty bars and restaurants, making it a great escape near Boston for foodies.

Hartford, CT

Hartford, Connecticut, is about a two-hour drive from Boston and features an abundance of historic sights, making it a perfect day trip for anyone looking to experience more of New England. Whether you’re interested in art, history, architecture, or literature, you’ll find it in Hartford.


Book lovers will adore the opportunity to visit the Mark Twain House and Museum. The community of Hartford converted the author’s home into a stunning museum.

The Mark Twain House features plenty of personal belongings and artifacts belonging to the author, including the original writing desk on which he wrote so many classics. The museum hosts a variety of events ranging from Mark Twain-themed beer tastings to literary events throughout the year.

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For another historical gem in Hartford, slide into the Harriet Beecher Stowe Center. Visitors can go inside her historic mansion, filled with authentic period-appropriate furniture. 

If you’re interested in fine arts, head straight to the Wadsworth Atheneum Museum of Art to browse its eclectic collection of 19th- and 20th-century American art.

Portland, ME

Travelers searching for fantastic shopping, exceptional seafood, and historic buildings should consider a day trip to the coastal city of Portland, Maine.


Portland is a two-hour drive or train ride from Boston and is home to some of the best seafood in New England. Portland is beautiful year-round, and the port city has become a popular tourist hot spot in recent years, attracting visitors from all over the world.

The historic district of Old Port features picturesque cobblestone streets, fabulous shopping, and a variety of restaurants and bars. Browse through the unique clothing boutiques, gourmet food stores, and gift shops while enjoying the classic New England beauty.

Foodies will love tasting various New England dishes like lobster rolls and clam chowder and unique delicacies like potato donuts. Wonderful waterfront dining options are available for seafood lovers who want to sample the catch of the day while gazing out on the harbor. You’ll find plenty to eat, drink, and buy for every taste and style in Portland, ME.


Ryan O'Rourke is a seasoned traveler and the founder & editor of Treksplorer, a fiercely independent guide to mid-range luxury travel for busy people. With over 20 years of extensive travel experience, Ryan has journeyed through over 50 countries, uncovering hidden gems and sharing firsthand, unsponsored insights on what to see & do and where to eat, drink & stay. Backed by his travel experience and in-depth research, Ryan’s travel advice and writing has been featured in publications like the Huffington Post and Matador Network. You can connect with Ryan on Twitter/X at @rtorourke.

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