Top Best Small Towns in Massachusetts

1. Northampton, 2. Provincetown, 3. Concord, 4. Wellfleet, 5. Sandwich, 6. Sturbridge, 7. Gloucester, 8. Rockport, 9. Westport, 10. Lenox. Massachusetts is well-known for many things, including its delicious clam chowder, stunning fall foliage, and rich history. It is also famous for its incredibly charming small towns that are simply perfect. Everything from the distinctive architecture to the cozy local shops leaves an indelible impression. Let's discover the best small towns in Massachusetts now.

  1. Northampton
  2. Provincetown
  3. Concord
  4. Wellfleet
  5. Sandwich
  6. Sturbridge
  7. Gloucester
  8. Rockport
  9. Westport
  10. Lenox


Exploring new areas of this wonderful state is a lot of fun. Northampton is a lively and colorful town that you should definitely visit. This Hampshire County community has a little bit of everything, and it’s easy to see why residents think everyone should move here. Northampton has it all: amazing shows, delicious chocolate, great outdoor opportunities, and small-town New England charm. Northampton is well-known for its artistic atmosphere. It’s packed with musicians, academics, and various artists. This is a lovely town for a stroll, but there’s plenty to do if you want to spend a day or weekend exploring.

Going downtown is the best way to get a sense of the community’s flavor. There are numerous charming specialty shops, cozy bookstores, excellent restaurants, and plenty of people-watching opportunities. For a cheap read, go to Raven Used Books. Great books can easily be found for a dollar each. For a sweet treat, stop by Ben & Bill’s Chocolate Emporium. It’s a wonderful family-run chocolate and ice cream shop. The town is awash in vibrant expressions of art and culture. Then, stretch your legs by biking the beautiful Norwottuck Branch Rail Trail. It’s a great way to get some fresh air and enjoy the natural beauty of the area.

top best small towns in massachusetts

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top best small towns in massachusetts

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Massachusetts has it all: cities and small towns, beaches and mountains, natural beauty, and, of course, history. Provincetown is a day or weekend trip destination that encompasses some of the best of what the Bay State has to offer. This tiny historic beach town, located at the very end of the Cape Cod peninsula, has plenty to see, do, and explore. Since the turn of the century, Provincetown, Massachusetts, also known as “P-town”, has been a popular summer beach resort destination. The year-round population of just under 3,000 people grows to around 60,000 during the summer months.

Provincetown has evolved into not only a premier resort destination in New England, but also a destination for artists, writers, families, the fishing community, and the LGBTQ+ community. It’s a one-of-a-kind destination that everyone can enjoy. The town has a very long history that dates back to the 1600s. Although Plymouth is often given all of the credit for the Pilgrims and the Mayflower, the ship first landed in the New World in November 1620 in Provincetown. A visit to Provincetown would be incomplete without a walk along the historic MacMillan Pier. This is where you can take a ferry, go whale watching, or charter a boat. It was built in 1956.

Hundreds of tiny colorful shacks line the pier and serve as tourist shops during the high season. Commercial Street is the main thoroughfare through P-town. It is home to dozens of shops, restaurants, and historic structures such as Whalers Wharf, Provincetown Public Library, and Provincetown Town Hall.

top best small towns in massachusetts

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top best small towns in massachusetts

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Concord is steeped in literary and Revolutionary War history. The “shot heard “round the world” was fired here on the North Bridge in 1775, and the area is rife with other historic landmarks from the early days of the Revolutionary War. Concord is also associated with several great American authors, including Henry David Thoreau, who immortalized nearby Walden Pond during his solitary stay here. The Concord Museum is the best place to learn about the town’s most important sites and residents, as well as the Native Americans who came before European settlers.

A Paul Revere lantern, one of the two legendary lights that alerted the revolutionaries to the British attack, is among its most important collection items. Thoreau’s writing desk and other personal items, as well as a recreation of Ralph Waldo Emerson’s study and other period rooms, are among the other exhibits. Literary tourists can visit several significant sites, including the author’s former home, the Ralph Waldo Emerson House. He entertained other prominent writers and thinkers of his time, including Thoreau and Louisa May Alcott, while living here, and it was here that he wrote his famous essay Self-Reliance. Another popular attraction in Concord is Thoreau’s cabin on Walden Pond, which also has a visitor center. Visitors can pay their respects to some of Concord’s great writers, including Emerson, Thoreau, and Alcott, as well as Nathaniel Hawthorne, at Sleepy Hollow Cemetery, also known as Author’s Ridge.

top best small towns in massachusetts

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top best small towns in massachusetts

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One of the best parts of visiting Massachusetts is its abundance of charming small towns. All of these small towns have a lot to offer, but the one of most popular is Wellfleet. This beach town has so many attractions that it is ideal for a family vacation. Wellfleet is a charming and quaint Massachusetts town located between the tip and the elbow of Cape Cod. It’s ideal for a family day trip. Although small, downtown Wellfleet has a wonderful selection of restaurants, shops, and galleries, and visitors can catch a show at the Wellfleet Harbor Actors Theater (WHAT), which features all types of performing arts.

The beaches in Wellfleet are one of its main draws, and there are many to choose from. The majority of the beaches are on Wellfleet Harbor, a well-protected area with calmer waters that is popular with families with children. Cahoon Hollow Beach and Lecount Hollow Beach (also known as Maguire Landing Beach) are two of the most popular beaches, both of which have lifeguards and some amenities. Indian Neck Beach, popular with families, and Mayo Beach, which has free parking and is known for its seashells, are two smaller beaches. On the way back to the mainland, stop in Yarmouth to see the Whydah Pirate Museum, which houses the world’s only confirmed pirate ship artifacts.

top best small towns in massachusetts

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top best small towns in massachusetts

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Sandwich, located on Cape Cod’s northern shore, does not necessitate the long drive or ferry ride required by many of the other towns. Its beaches are known for their safe waters because they are nestled deep within Cape Cod Bay. Beautifully preserved centuries-old homes demonstrate the current owners’ tender care. In the Village Center, a working gristmill stands next to one of the oldest Town Halls in the United States. As you travel out of town, scenic back roads take you to cranberry bogs, salt marshes, and breathtaking views of Cape Cod Bay.

Sandwich was a major center for glassmakers during the nineteenth century, and those interested in local history can visit the Sandwich Glass Museum, which houses thousands of examples of authentic Sandwich Glass, as well as exhibits about the craft and live demonstrations. Visitors can also see demonstrations at the Dexter Grist Mill before purchasing a bag of stone-ground flour. Sandwich is also home to the Heritage Museums and Gardens, a unique collection of museums dedicated to Americana. The buildings are surrounded by 100 acres of gardens and are linked by walking paths, allowing visitors to enjoy the flowers, particularly the hydrangeas and rhododendrons, as well as an interactive play area for children. Among the museums are an art museum with Native American and colonial folk art, an automobile museum with classic cars, and others.

top best small towns in massachusetts

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top best small towns in massachusetts

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Old Sturbridge Village is a popular Bay State historical attraction that allows visitors to walk through a recreated colonial village without using a time machine. Old Sturbridge Village is a one-of-a-kind way to relive history. This living history museum recreates rural Massachusetts life from the 1790s to the 1830s. It is New England’s largest such attraction, spanning an incredible 200 acres. Visitors are completely immersed in early-nineteenth-century life, including a rural farming community, a neighborhood centered on a water-powered sawmill, and a bustling village center. You can wander through 59 antique buildings with period furnishings, three water-powered mills, and streets that are exactly as they were hundreds of years ago.

Visitors can immerse themselves in the village activities by listening to costumed interpreters speak in modern English. Tourists can interact with the costumed interpreters, observe them going about their daily chores and various occupations, and even participate in some areas. Throughout the year, various special events are held. Wells State Park, a dog-friendly public park with 12 miles of multi-use trails and a large pond for kayaking, fishing, and swimming, is also located in Sturbridge. There is also a small nature center and day use facilities, such as grills and picnic pavilions, for visitors to enjoy.

top best small towns in massachusetts

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top best small towns in massachusetts

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Gloucester is a city in the United States’ Essex County, Massachusetts. It is located on Cape Ann and is part of the North Shore of Massachusetts. This town is the perfect blend of history and modern excitement, with amazing places to eat, shop, and explore. Gloucester, America’s oldest seaport, is only a scenic train or car ride north of Boston. Annisquam Light, pictured above, has been guiding sailors’ home for over 200 years. Today, it’s an excellent location for a few scenic shots. Its beautiful beaches, hemlock forests, and green parks have inspired artists for generations – it is the continent’s oldest working art colony. Visit the Cape Ann Museum to get a taste of coastal New England’s rich artistic history. The exhibits feature work by both past and present local artists.

You should begin your visit to this seaport at the harbor. Explore this historic working seaport’s sights, sounds, and smells. While you’re there, pick up some of the freshest fish you can find. If all that fresh air and strolling whets your appetite, Seaport Grille serves delicious and generous portions of lobster fare. You won’t have to worry about finding street parking or feeding a meter because the restaurant has a large, free parking lot. The Fishermen’s Memorial on Cape Ann is one of Gloucester’s most recognizable landmarks. It contains the names of fishermen who died at sea since the 1700s.

top best small towns in massachusetts

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top best small towns in massachusetts

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Rockport is a pristine coastal town on the Cape Ann peninsula. It’s known for its beautiful blue waters, classic clapboard harbor shacks, delectable seafood, and down-home charm. Because of the idyllic beauty of this coastal New England town, Rockport is home to many artists, whose work can be seen in the town’s many galleries. The Rockport Art Association and Museum, which features changing exhibits highlighting local art, including film and other media, is also open to visitors. Rockport values the performing arts, which can be found at The Shalin Liu.

Rockport, located at the tip of Cape Ann, is also home to several beautiful beaches and scenic oceanside parks, including Halibut Point State Park. The Straitsmouth Island Lighthouse and the Twin Lighthouses of Thatcher Island are two local lighthouses that can be seen from one of the many sightseeing cruises available. The Captain’s Bounty on the Beach is an excellent choice for those looking for a beachfront hotel that offers pet-friendly rooms and efficiency suites. Rockport is teeming with small art galleries and family-run businesses selling everything from locally-made soap to stunning vintage gowns. When your stomach grumbles, head to a local eatery for classic seafood near the water, such as the Red Skiff Restaurant or Roy Moore’s Fish Shack Restaurant.

top best small towns in massachusetts

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top best small towns in massachusetts

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Westport is a small town in Bristol County, Massachusetts, on the state’s southern coast. Westport, once a prosperous seafaring town and cotton mill community, has transformed into a quiet coastal town with plenty of natural beauty and a truly stunning beach reservation. Continue reading to find out why you should visit this hidden beach town this summer. The amount of farming that takes place in Westport distinguishes it from other beachside communities in Massachusetts.

Westport Town Farm is a 40-acre open space and historic farm that is breathtakingly beautiful. This scenic spot along the Westport River features beautiful hiking trails, an antique farmhouse, a full dairy barn, and stone walls dating back to the early days of America. Visit for some great picnicking or to see the working farm that grows food for those in need. Of course, no trip to Westport is complete without a day at the beach. Horseneck Beach State Reservation is an 800-acre coastal park off the coast of Westport. This beautiful beach is a protected habitat, and its natural beauty is unspoiled. It’s one of the few places in Massachusetts where you can camp right on the beach, and the scenery is breathtaking. There are also numerous hiking and biking trails, as well as opportunities to fish, windsurf, and boat.

top best small towns in massachusetts

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top best small towns in massachusetts

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If you’re looking for a getaway destination in Massachusetts this fall, Lenox is the place to be. There’s plenty to see and explore in this lovely mountain town, which has a rich history rooted in the Gilded Age and incredible Berkshires scenery. Lenox is a small town with a population of around 5,000 people. Tanglewood, Shakespeare & Company, and numerous historical sites are located in the Berkshires in Western Massachusetts, near Pittsfield. Fall foliage in Lenox is incredible to see, especially in October when it is at its peak, surrounded by the natural beauty of the Berkshires. Hike through the grounds of Mass Audubon’s Pleasant Valley Wildlife Sanctuary to reach Lenox Mountain.

Lenox became a Gilded Age resort town for the wealthy, who built imposing mansions throughout the town between 1880 and 1920. Several of these residences have been preserved and converted into museums or inns. The Mount, Edith Wharton’s home, was designated a National Historic Landmark in 1971 and is one of the most impressive historical sites. The American author’s 1902 Gilded Age mansion is set on 50 acres and has two gardens to explore. Ventfort Hall Mansion and Gilded Age Museum is a Jacobean Revival-style mansion built in 1893 for J.P. Morgan’s sister. Self-guided tours of the mansion and grounds are available. In the fall, the museum also hosts a Halloween event and a Paranormal Investigation.

top best small towns in massachusetts

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top best small towns in massachusetts

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