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Top Boston Day Trips For Every Explorer

Steve Jennifer
Updated: May 17, 2024

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Boston, a city steeped in history, is also a fantastic starting point for exploring the rich surroundings of New England. Just a hop, skip, and a jump away, numerous captivating destinations await those ready to venture beyond city limits. Whether you're a history buff, nature lover, or culinary enthusiast, these nearby spots offer a perfect escape from the urban hustle.

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01. Salem, Mass

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Salem’s history is intertwined with the notorious witch trials of 1692, making it a fascinating destination for those intrigued by the past. Tour the Witch House, once the residence of Judge Corwin, the trial judge, and immerse yourself in the eerie history that still haunts the town. Literary fans can explore Nathaniel Hawthorne’s home, bringing to life the settings of his gothic tales. While Halloween is the peak season, Salem’s mystic charm is captivating year-round.

02. Provincetown, Mass

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For seafood aficionados, Provincetown is a must. Dine at the famed Lobster Pot where the catch of the day is always fresh and the ocean views are complimentary. For a panoramic perspective, climb the Pilgrim Monument, which offers breathtaking vistas from over 200 feet above sea level. Provincetown’s vibrant atmosphere and stunning coastal scenery make it an ideal destination for a day away from Boston.

03. Plymouth, Mass

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Plymouth holds a special place in American history, marked by the legendary Plymouth Rock. Beyond the rock, the Pilgrim Hall Museum offers a fascinating insight into the lives of America's early settlers with artifacts dating back to the Mayflower's voyage. Plymouth’s laid-back charm and scenic landscapes make it an excellent choice for a relaxing day trip, especially when New England’s weather shines its brightest.

04. Concord, Massachusetts

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Less than an hour’s drive from Boston, Concord beckons with its deep literary and revolutionary history. It's the home of the Minute Man National Historical Park, where the first battle of the American Revolution took place. Literary buffs can visit the homes of Ralph Waldo Emerson and Louisa May Alcott, where much of America’s beloved literature was penned. The tranquil beauty of Walden Pond, which inspired Thoreau’s famous reflections, offers a peaceful retreat. Concord’s blend of history and natural scenery makes it an enriching day trip for those looking to escape the city’s bustle.

05. The Basketball Hall of Fame

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Just a 90-minute drive from Boston lands you in Springfield, Massachusetts, the home of the Basketball Hall of Fame. This place is a slam dunk for sports enthusiasts, offering a deep dive into over a century of basketball heritage. With an impressive array of memorabilia from basketball legends, it’s a pilgrimage for fans of the sport. For anyone with even a passing interest in basketball, this destination in western Massachusetts is a real game-changer.

06. Newport, Rhode Island

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A drive to Newport, Rhode Island, offers a glimpse into some of America's grandest mansions, including the iconic Breakers and the famed Holiday House, owned by Taylor Swift. Newport, often dubbed the Ocean State, boasts the scenic Cliff Walk, where the views of the Atlantic are nothing short of spectacular. Don’t miss dining at the White Horse Tavern, which prides itself on being the oldest restaurant in America, adding a historic flavor to your visit.

07. Portland, Maine

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Head to Portland, Maine, for more than just their celebrated lobster rolls. This city is a treasure trove of culture with its Portland Museum of Art, housing over 22,000 works and a history dating back to 1911. The Old Port district, with its quaint cobblestone streets and historic warehouses, transports you back in time, while also offering some of the finest dining in Maine. And of course, a visit to Portland wouldn’t be complete without checking out its picturesque lighthouses

08. Mystic, Connecticut

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Mystic, Connecticut, about a two-hour drive from Boston, is a maritime lover’s dream. The Mystic Seaport Museum showcases America’s seafaring past with a collection of historic sailing ships and a recreated 19th-century seafaring village. Don't miss the chance to explore the Mystic Aquarium, where sea life, including beluga whales and penguins, delight visitors of all ages. The town’s charming downtown area, with unique shops and seafood restaurants, invites leisurely exploration after a day of maritime adventures.

09. Martha’s Vineyard, Massachusetts

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Escape to Martha’s Vineyard for a taste of island life. Just a ferry ride from Cape Cod, this idyllic island offers a blend of upscale charm and casual beach vibes. Explore the colorful gingerbread cottages of Oak Bluffs and the stately lighthouses dotting the coastline. The island's vineyards provide a perfect backdrop for a leisurely afternoon of wine tasting. With its stunning beaches and quaint town centers, Martha’s Vineyard is a picturesque getaway from the everyday.

10. Stowe, Vermont

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For a taste of European charm without leaving New England, head to Stowe, Vermont, a three-hour drive from Boston. Known for its ski resorts, Stowe is equally enchanting in the off-season with its Alpine-inspired architecture and vibrant fall foliage. The town offers a variety of outdoor activities, from hiking to biking, which showcase its stunning natural landscapes. Culinary enthusiasts will enjoy the local cheese and maple syrup that epitomize Vermont’s artisanal food scene. Whether covered in snow or bathed in autumn color, Stowe provides a refreshing change of scenery with a touch of Old World elegance.

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