The 7 Friendliest Little Towns In Massachusetts

Since its founding as a colony in 1630, Massachusetts has refined the art of hospitality, with its small towns among the friendliest. Provincetown, for example, shares its culture with visitors through annual Portuguese festivals and international film festivals. Chatham, on the other hand, celebrates the summer with Friday night band concerts and juried craft festivals. Some of the friendliest fishermen can be found in Wellfleet, which hosts the annual Wellfleet OysterFest and a seasonal farmers' market where visitors can pick up plenty of local treats and fresh seafood. If you are looking for the friendliest towns in Massachusetts, these seven are sure to leave you in great spirits this year.

Edgartown

Established in 1671, Edgartown was the first colonial settlement on Martha’s Vineyard, resulting in centuries of community heritage. The town hosts an extensive annual calendar of events, including the Edgartown Village Market in June, an open-air market in the historic downtown district where local vendors sell produce, flowers, and crafts. Come July, you can also attend Edgartown’s 4th of July fest, which features a parade and fireworks that overlook the harbor. Community spaces are also abundant, such as Mytoi, a 14-acre Japanese garden located just east of Edgartown on Chappaquiddick Island. Here, you can appreciate Japanese maples, pines, and flowering shrubs that reflect traditional Japanese gardening techniques.

Provincetown

For nearly three centuries, Provincetown has welcomed people of diverse backgrounds, with writers, artists, Portuguese immigrants, fishermen, whalers, and members of the LGBTQ+ community among the groups who have called the town home. It is also one of the country's oldest continuous art colonies, with many festivals and institutions rooted in this history. In June, for example, the town welcomes more than 80 American and international independent films, screening them over five days at the Provincetown International Film Festival. Later in the month, the Provincetown Portuguese Festival takes place, celebrating the heritage of its Portuguese immigrants through traditional attire, food, dance, and more. The Provincetown Art Association and Museum (PAAM) is the perfect place to explore the town’s art scene, exhibiting over 5,350 pieces of work that represent the Cape’s artistic history.

Lenox

Home to the estate of famed novelist Edith Wharton, Lenox is a creative hub in the Berkshires that enjoys sharing its art and culture with visitors. Travelers can kick off their trip in Lenox by visiting Wharton’s very estate at The Mount. In addition to touring the home where she once lived, guests can attend a variety of cultural programs, including author talks, readings, and lectures. Those visiting in the summer months can also visit Tanglewood, the Boston Symphony's summer home, which offers public performances and recitals. The fall season, meanwhile, brings events like the Lenox Apple Squeeze, a fall fest with over 70 vendors, family fun, music, and a carnival for the kids.

Chatham

Chatham truly comes alive in the summer months, welcoming residents and visitors from across the region to summer concerts and art fairs. Every Friday, from July through the beginning of September, the town hosts the Chatham Band Friday Night Concerts, with each evening consisting of a live concert, right down the street from the Chatham Fish Pier and the lighthouse. Another highlight is the Chatham Summer Craft Festival, which takes place over two days at the beginning of August, featuring juried artisans and specialty food vendors. A few of the items you can browse here include handmade jewelry, art, home decor, gifts, and bath and body products. While in town, plan an afternoon at the Monomoy National Wildlife Refuge, which covers thousands of acres and was established in 1944 as a nature sanctuary for migratory birds.

Wellfleet

The Massachusetts Cultural Council designated the Wellfleet Cultural District in 2017, recognizing much of Wellfleet’s maritime history, art, and culinary scene. There are several notable festivals in the area, including the Wellfleet Oyster Fest, one of the most popular. This year, the festival will take place on October 17th and 18th, with over 20,000 people attending to savor Wellfleet’s beloved oysters. Over the course of two days, live music fills the streets, along with arts and craft vendors, local food and drink, and plenty of oysters! For even more local food, you can also stop by the Wellfleet Farmers Market, which takes place on Wednesdays between mid-May and mid-October. Local produce, fish, meat, eggs, cheese, flowers, honey, and teas are among the items you can purchase from the friendly vendors. To try some of Wellfleet’s delicious food, grab a meal at Winslow’s Tavern, which is open seasonally each year. Located right in the heart of town, it serves a delicious array of seafood, pasta, meat, and burgers.

Shelburne Falls

Shelburne Falls is home to a fascinating trolley history and actively shares this heritage with visitors. A trolley bridge was built in 1908 and became obsolete by 1927 as motorized vehicles became more popular. Just a couple of years later, in 1929, the Shelburne Falls Women's Club came together to transform the old structure into the Bridge of Flowers, which travelers can still visit today! To learn more about the role of the trolleys in Shelburne Falls’ early days, you can also check out the Shelburne Falls Trolley Museum, where guests can ride one of the historic trolleys or play with wooden or electric trains. Each fall, the museum also hosts Trolleyfest, an annual event that celebrates the restoration of one of the trolleys with caboose rides and trolley-era demonstrations such as butter making, cider pressing, blacksmithing, and cow milking.

Stockbridge

Stockbridge is filled with community spaces and gardens that bring both residents and visitors together to enjoy time with their loved ones. Naumkeag is one of the most renowned spaces, a public garden and estate covering 48 acres and dating back to the late 19th century. Between April and May, the Daffodil and Tulip Festival takes place at Naumkeag, where eight acres of gardens burst into color with spring bulbs and seasonal decorations, along with extras like a pop-up plant sale, snacks and refreshments, and a seasonal gift shop. Other highlights include the Berkshire Botanical Garden, one of New England’s oldest botanical gardens, encompassing 24 acres and showcasing dozens of unique garden spaces.

The Refreshing Spirit Of A Massachusetts Small Town

Few things are as refreshing as a spirited small town. And in Massachusetts, you certainly won’t have a hard time finding one that delivers this hospitality. Some, like Wellfleet, are particularly inviting for the culinary scene, while others, like Shelburne Falls, are eager to share their history with visitors. However, they all undoubtedly share the trait of being some of the most heartwarming places to visit in the Bay State!