7 Coziest Small Towns in Massachusetts

While most people’s definition of “cozy” will vary based on personal preferences and life experiences, few would argue against the fact that this adjective perfectly describes many of the best places to visit in Massachusetts. This is especially true of the state’s small communities, each of which oozes that sense of warmth, comfort, and safety that makes them such charming and yes, cozy, destinations to explore.

It certainly helps that this region of New England is home to some of the oldest communities in the USA. Here, historic architectural flourishes, like those seen on the whimsical old houses of Oak Bluffs on Martha's Vineyard, create a sense of organic rather than manufactured growth that simply makes you feel good.

Find out more about the coziest small towns in Massachusetts as we dig a little deeper and explore the “Bay State.”

Falmouth

While one of the larger towns on this list, its lovely Cape Cod setting certainly adds a great deal of that unique New England charm to Falmouth. Settled in 1660 and named after the picturesque fishing village in England, Falmouth, MA, exudes a cozy village-like appeal that’s heightened by the many unique boutique shops, galleries, and cafés that fill the downtown core and draw tourists to the area.

The village is especially lively in the summer, with the weekly farmer’s market and regular arts and crafts fairs bringing friendly local artisans to town to share the fruits of their labor. To capture a few unforgettable memories of your cozy Cape Cod adventure, get your phone out and take a selfie with the picturesque Nobska Lighthouse as a backdrop.

Sturbridge

Sturbridge is steeped in history and tradition and is a captivating destination for visitors looking to step back in time for a day. Located mid-way between the cities of Springfield and Worcester, the best things to do in Sturbridge are to be found in Old Sturbridge Village, the largest outdoor living history museum in the Northeast. Here you’ll have the opportunity to experience authentic rural New England as it would have been in the 1830s, complete with costumed guides showcasing traditional crafts and country living as it once was.

Sturbridge Town Common adds to the town's historic ambiance and is the scene of fun seasonal festivals and events that celebrate the town’s rich heritage.

Gloucester

Gloucester is set on the Cape Ann peninsula and while only a 45-minute drive from the big city of Boston, its beautiful, rugged scenery feels a million miles away. One of the country’s oldest still-bustling harbors with roots going all the way back to the 1640s, the town’s deep connection to the sea is everywhere evident. Highlights of this coastal heritage include the Eastern Point Lighthouse overlooking Gloucester Harbor, and fascinating whale-watching tours that provide an opportunity to get up close to some of the area’s most fascinating marine life.

Gloucester is also a gateway to the stunning beaches of Cape Ann, popular spots for a little relaxation or from which to explore the beautiful New England coastline. That cozy coastal vibe is also very evident in Gloucester’s downtown area, home to artist studios, galleries, and many festivals and events that celebrate its unique heritage and community spirit.

Plymouth

Plymouth is another quaint community that owes its name to an English coastal town. Referred to fondly as "America's Hometown" for having been the site where the first Pilgrims disembarked the Mayflower in 1620, you can get a flavor of this important historic event at Plimoth Plantation. Part of the Plimoth Patuxet group of attractions, this interesting living history museum paints a realistic portrait of what life was like for these first settlers in the 17th century with re-enactments of daily colonial life. It also provides insights into the experiences of the Native Wampanoag people, too, during this period.

Be sure to visit the famous Plymouth Rock, an important landmark that serves as an emblem of the courage of the first English settlers in New England. You can also climb aboard a replica of the Mayflower, which shares details of the harrowing journey.

Salem

There’s little doubt that pretty Salem has shed the notoriety associated with the infamous witch trials that took place here in 1692. While you can explore this aspect of the town’s past in attractions such as The Witch House, home of trial judge Jonathan Corwin, and the Salem Witch Trials Memorial, you don’t have to try too hard to find other important relics of the town’s past.

The Peabody Essex Museum, for example, is a must-visit. One of the oldest continuously operating museums in the USA, here you’ll find examples of local and international art that explore Salem's rich maritime history as one of the country’s most significant ports. The Salem Maritime National Historic Site also celebrates the town’s seafaring legacy, featuring historic buildings, wharves, and a replica of the trading ship Friendship.    

Oak Bluffs

Oak Bluffs is a charming, cozy coastal town located on the northeastern shore of the famous island of Martha's Vineyard. Accessible only by ferry from Falmouth or New Bedford, Oak Bluffs' iconic gingerbread cottages date from the 1800s and feature intricate, colorful flourishes that create a fairy-tale-like ambiance. The town’s cozy magic can also be experienced with a ride on the Flying Horses Carousel, a much-treasured local attraction dating back to 1876 and recognized as the oldest platform carousel in the United States.

Cultural activities in Oak Bluffs also add to its allure. Highlights include outdoor concerts, art galleries, and the annual Sankofa Festival, a popular literature and culture event that celebrates the town's historical significance to the African American community.

Shelburne Falls

Located in northwest Massachusetts just a short drive from the state border with New Hampshire, the picturesque village of Shelburne Falls owes its charm to the Deerfield River, which separates the town from the neighboring community of Buckland. It’s here you’ll find one of the most picturesque cozy corners of the state: The Bridge of Flowers.

This exceedingly charming attraction was a former trolley bridge built in 1907 connecting the two towns. Now a pedestrian bridge, it’s adorned with plants and blooms that, when in season, make for a wonderful photograph. You’ll also find the bridge captured in the work of the many artists and craftspeople of the Shelburne Falls Artisans Cooperative who operate the quaint shops and galleries dotting both towns.

The Final Word

From the seaside setting of Gloucester and the maritime heritage of Plymouth where America's early history comes so vividly to life, the coziest towns in Massachusetts offer plentiful excuses for travellers to stop in and explore. Learn more about these and other must-visit New England communities on our list of seven cozy small towns in Massachusetts that are waiting to welcome you.