10 Charming Small Towns to Visit in Massachusetts

Massachusetts is home to roughly seven million individuals dispersed across 10,565 square miles, but only some live in its busy metropolises like Boston, Worcester, and Springfield. The state has hundreds of smaller communities worth exploring, from best small towns in massachusetts to live attractive beach settlements to historic mountain towns.

Want to get to know the state’s small towns better? Here are 10 cities in Massachusetts worth planning a whole trip around.

best small towns in massachusetts to visit

Provincetown

Provincetown has long been a hot summer spot for Massachusetts locals and out-of-state tourists. And though it’s a very famous place, it’s still a small town, with less than 3,000 people calling it home year-round. Enjoy its beaches, its beloved Pride events, and its arts and culture scene, including its excellent galleries in summer, fall, winter, and spring.

Concord

Concord, one of the state’s most accessible little towns, is only 20 miles outside of Boston. The town’s most famous features are its idyllic parks, such as Walden Pond, which inspired several renowned American authors, including Ralph Waldo Emerson and Henry David Thoreau, who both made Concord home. 

Northampton

With over 29,000 residents, Northampton is arguably the “largest” of the little towns on the list, but that doesn’t make it any less endearing. Situated in the state’s western region, this town boasts a thriving arts scene, with various live music venues, local businesses, and the Northampton Museum and Art Gallery.

Rockport

Returning to Massachusetts’Massachusetts’ east coast, visitors can explore the quaint town of Rockport, which is home to less than 8,000 people and is located at the point of Essex County. The city provides plenty of beach and woodland hikes and year-round dining and retail possibilities for those who like to get outside and discover the natural world.

Williamstown

In the northern part of the state, travelers will discover the quaint village of Williamstown. Thanks to the Clark Art Institute, which hosts an annual impressionist and contemporary artwork exhibition, it has another modest but significant presence in the art world. Because the village is situated right on the Appalachian Trail, hikers may also be familiar with it.

Sandwich

When you get to the Cape, travel to Sandwich, the oldest settlement on the peninsula. As people age, their beauty also becomes more historical. Visitors can explore historical sites like the Hoxie House Museum, which dates back to about 1675 and is probably the oldest saltbox house on Cape Cod. Not to be missed are the renowned Sandwich Glass Museum and the Heritage Museums and Gardens.

Stockbridge

Enjoy a picture-perfect vacation in Stockbridge. The renowned American painter Norman Rockwell, who lived in this tiny Berkshire village, was greatly influenced by its breathtaking beauty. Visit the Berkshire Botanical Garden to explore the carefully manicured flora or lush natural settings, and don’t miss the opportunity to witness a performance by the Berkshire Theatre Group.

Oak Bluffs

Visit the charming tiny town of Oak Bluffs on the island of Martha’sMartha’s Vineyard and dip your toes in the sand. The two-mile Joseph Sylvia State Beach, which gained notoriety from the movie “Jaws,” is arguably the community’s-community’s most well-known feature. The Obamas are regular summer residents of the enclave, also an A-list sanctuary.

Nantucket

Visit Nantucket, a secluded island past Martha’s Martha’s Vineyard, for one last island getaway. The island, which has just over 11,000 permanent residents, is modest but has a rich historical legacy. In particular, Great Point, Sankaty Head, and Brant Point are three historic lighthouses that are open for guests to view. Along with the best small towns in massachusetts to live fantastic boutique shopping, there are plenty of seafood restaurants for visitors to enjoy. 

Westford

Did you know best small towns in massachusetts to live offers skiing? Go to Westford to make your determination. The Nashoba Valley Ski Area is located near the border with New Hampshire in the northern section of the state, providing excellent skiing conditions. Because of its hiking and biking paths and attractions like The Butterfly Place, an indoor habitat for butterflies from all over the world, it is a year-round destination.

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