12 Of The Most Welcoming Towns In Massachusetts
Where the first railroad in America, the first telephone call, and the first battles of the American Revolutionary War all occurred, the state of Massachusetts has seen and experienced it all. Fortunately for you, some of the most welcoming towns in Massachusetts provide beautiful community engagements and festivities in a land whose Native American name means “at or about the Great Hills.” Each of these destinations is not only historically relevant and naturally appealing, but they are also popular for their cultural nuances and events that you can participate in or observe. This year, give yourself a chance to explore the most welcoming towns in Massachusetts for their community spirit and their continued legacies of the past.
Salem
Just about 25 miles north of Boston lies the town of Salem, often painted in the prism of its tragic past yet brimming with living history. The most endearing and enchanting event that one can attend is the annual Haunted Happenings, the largest celebration of Halloween in the US, where parties, parades, vendor fairs, walking tours, and other amenities can be experienced within the month of October. Other yearly events include the Salem Arts Festival in June, when the local creative community engages in live performances, maker marketplaces, interactive art, murals, and exhibitions in preparation for the festive Halloween. Meanwhile, the Salem Maritime Festival, held in August at the Salem Maritime National Historic Site (Derby Wharf area), features historic building tours, food trucks, lawn games, and the fun “Great Salem Cardboard Boat Regatta” where teams build boats from cardboard and duct tape to race in the harbor. Despite its morbid past, Salem now welcomes and entreats newcomers to the fantastic and spooky delights of the present.
Rockport
Rockport is a charming seaside town offering more than lobster rolls and seaside views—its festival calendar includes summertime events like the Rockport Chamber Music Festival, occurring in different months of the year and bringing music and other artistic genres to audiences in the greater Boston area and the Massachusetts North Shore. Meanwhile, the Rockport Celtic Festival at the Shalin Liu Performance Center is where chamber music and Celtic traditions create a magnificent ambiance for the whole town. Finally, there is the beloved Rockport Harvest Fest in the fall, which celebrates the autumnal season with local food, live music, vendors, and coastal scenery. Visiting Rockport during these events gives you not just the coastal tranquility, but lively local culture and seasonal excitement to boast about.
Concord
Concord’s festival lineup reflects its blend of history, literature, and strong community roots. In the fall, you will find the Concord Festival of Authors (often from October to November), which draws writers and readers to literary conversations throughout town. There is also the Musketaquid Earth Day Festival each April, organized by the Umbrella Arts Center, which combines environmental awareness and natural motifs with arts and community parade events. For visitors curious to know more of the community’s historic roots, the Patriots’ Day Reenactment each April commemorates the early battles of the American Revolution with reenactors and town-wide events. These gatherings make Concord more than a historic landmark—they make it a living, engaged community worth spending a visit on the weekends or on any other day of the year.
Lenox
In the heart of the Berkshires, Lenox invites visitors to join its seasonal celebrations that blend culture, outdoor life, and communal arts and artists in a naturally appealing setting. Among the highlighted activities to seek out is the annual Lenox Winterland & Holiday Market, a multi-day event in early December featuring a tree lighting, craft market, ice skating, and winter whimsy in the town’s downtown. Meanwhile, the Lenox Summer Arts Festival that often occurs in June hosts more than 50 juried artists showcasing their fine arts and fine crafts in various media, including painting, photography, sculpture, jewelry, fiber, wood, metal, glass, and mixed media. Best of all is the Lenox Farmer’s Market, transpiring from May 23 through September 12, which sees food vendors, live musicians, and artists bringing vivacity and joy to the town. As a cultural retreat, Lenox stands out because you can pair elegant festival experiences with natural beauty and affection.
Northampton
Northampton boasts a cornucopia of arts, activism, and community energy with a host of events to participate or observe near the Connecticut River. The Paradise City Arts Festival, which occurs in both the spring and the fall, showcases top-tier craft and fine art pieces while drawing visitors into the vibrant downtown scenery. Meanwhile, the Hampshire Pride Parade & Celebration, transpiring on the first Saturday of May, highlights diversity and inclusion with one of the region’s most visible community gatherings. Finally, for a winter treat, First Night Northampton is a 12-hour arts-filled New Year’s Eve festival that brings families and friends together downtown from noon to midnight. A visit to Northampton during one of these events will show you how alive and vibrant the town is, amongst other welcoming towns in Massachusetts.
Westford
Westford enchants and enamors newcomers with its homely warmth and vibrant local celebrations. Each June, the town bursts into flavor at the Strawberries ‘N’ Arts Festival, where downtown transforms for artisan markets, live music, handmade crafts, and, of course, plenty of strawberry shortcakes. In May, the Apple Blossom Festival brings families together in a sunny community spirit and disposition, with parades, craft vendors, and outdoor fun for friends and families alike to enjoy. You should also keep an eye on the Patriots’ Day Candlelight Tribute at Westlawn Cemetery in April, when the townsfolk honor the brave men from Westford who served during the American Revolutionary War. Together, these gatherings show why people make the trip to Westford: it is not just a stopover, but rather a homely and hospitable destination that honors the traditions and ideals of Massachusetts.
Provincetown
At the tip of Cape Cod, travelers will come across the historic town of Provincetown, a vibrant destination celebrated for festivals that are bold, inclusive, and world-renowned. In late June, the Portuguese Festival & Blessing of the Fleet honors the town’s fishing and Portuguese immigrant heritage with music, dancing, food, and a boat blessing on the water. Meanwhile, during the Ides of August, you will find the flamboyant Carnival Week, featuring a major parade along Commercial Street and themed parties to participate in. Best of all, as one of the largest LGBTQ+-centric gatherings, TransWeek, formerly known as the Fantasia Fair, is a week-long transgender event that brings tens of thousands from around the globe in October to this small town for celebration, connection, and reaffirmation. These three-plus events are just some of the many activities and festivities that prove why people flock to Provincetown.
North Adams
Situated in the Berkshire foothills, the charming and accommodating town of North Adams surprises visitors with festivals that merge art, nature, and community in a gracious landscape. Each September, the acclaimed FreshGrass Festival at Massachusetts Museum of Contemporary Art (MASS MoCA) blends bluegrass, roots music, family workshops, and visual art across indoor and outdoor site-specific venues. Earlier in the year, specifically around October, you might encounter the Mill Town Circus, a theatrical-circus event inspired by New England mill towns, featuring acrobats, aerial acts, and a 'Mill Boss' Ringmaster for everyone to cherish long after the fun is done. In contrast, the Solid Sound Festival in June thrives and prospers as a multi-day music and art event also in the prestigious MASS MoCA. With so many festivities and fun to savor, North Adams is a paradisiacal and welcoming destination to revitalize yourself in a lush and soothing setting in the hills of Massachusetts.
Hudson
Hudson may appear modest on the map, but its calendar is rich with community engagement and social spirit to admire. During the month of September, the whole town shifts into festival mode for Celebrate Hudson, a free, downtown event with live music, food trucks, vendor booths, petting zoos, and rides—a true all-ages celebration of place and people. Earlier in spring, you can attend the annual HUDSON ArtsFest, a popular makers-market and artisan showcase highlighting local creativity. When the leaves turn red in the autumn, the Hudson Fall Festival & Car Show brings classic cars, autumnal vendors, and family fun to town—making Hudson worthy of a visit for those who want New England charm without the crowds. These community-driven events demonstrate why Hudson is one of the most welcoming towns to visit on the Assabet River.
Amesbury
The historic small town of Amesbury wakes up each summer with the beloved Amesbury Days, running from June 26 through July 4. For over a century, this multi-day festival has offered parades, block parties, pony rides, fireworks, and community cook-outs that celebrate the town’s endearing and enduring communities. One of the most special occasions of the Amesbury Days is the Amesbury Days Brewfest, which invites craft-beer lovers for outdoor sampling and live music. Another popular activity to try out is the Amesbury Winterfest & Holiday Parade, usually scheduled for late November, bringing festive lights, local shopping, and holiday engagement for everyone. As one of the most welcoming towns to visit in Massachusetts, Amesbury aims to please and accommodate everyone eager for recreational pursuits in the countryside.
Newburyport
By the Merrimack River and near the seacoast, Newburyport captivates newcomers during its signature festivals, among them the Yankee Homecoming, transpiring every July through early August, for which travelers can attend parades, waterfront concerts, artisan fairs, brewfests, and more in honor of Newburyport’s traditional history of reuniting family and friends in a welcoming community. In September, meanwhile, the Oysterfest in the Port of Newburyport dishes up shellfish from regional farms, spectacular performances, and other kinds of fun by the shore. Springtime brings the literate crowd to the Newburyport Literary Festival in April, featuring readings, author talks, and book-lover community-buzz. With its meaningful and exhilarating festivities, this New England town boasts plenty of communal spirit and enticement for everyone to enjoy.
Stockbridge
The welcoming town of Stockbridge beckons newcomers with a bevy of beautiful activities and landmarks that exude the communal spirit and livelihood of the Berkshires. The Chesterwood, open annually from May to October, is the historic home, studio, and gardens of America’s foremost late 19th early 20th-century sculptor, Daniel Chester French, who created the Lincoln Memorial. The homestead hosts yearly and varied exhibitions of French’s seminal and perennial works. Meanwhile, the Naumkeag, a 19th-century summer home, plays host to a slew of wonderful events such as the Naumkeag Pumpkin Show, which takes place in autumn, Winterlights in the winter, and the Daffodil & Tulip Festival in spring. Finally, the Berkshire Theatre Group provides a plethora of novel and classic performances that theater-goers and avid fans of timeless drama will definitely want to watch. With its festive events and curated performances tied to the historic and monumental landmarks of the area, Stockbridge connects all facets of the community into a seamless tapestry of comfort and delight.
Community Spirit Thrives in These Welcoming Massachusetts Towns
In the land “at or about the Great Hills”, travelers will come across some of the most welcoming small towns in Massachusetts, each one thriving from the shimmering Berkshires to the coastal dunes of the state. Many of these destinations celebrate seasonal pastimes and activities that revitalize one’s energy and spirits for another year of adventure and surprise. On the other hand, some commemorate their history, traditions, and cultural wonderment with festivities that remind us all of these small towns’ character. No matter the destination, these welcoming towns in Massachusetts are sure to treat everyone as friends and family in a state brimming with historic charisma and natural flair.
