8 Most Neighborly Towns In Massachusetts
With centuries of history, Revolutionary War heritage, and long-established art communities, the small towns of Massachusetts are uniquely united by their culture in ways few other states can match. While many of these towns, particularly the coastal ones, see an influx of tourists in the summer, it is the year-round residents who form the heart of these communities, fostering a strong sense of connection. Ready to unwind in one of these eight neighborly towns? You will be welcomed like a local and shown the town through their eyes.
Edgartown
With a population of just above 600 residents, Edgartown is one of the neighborly communities of Martha’s Vineyard. Each October, the community comes together to host the annual Martha’s Vineyard Food & Wine Festival, featuring Michelin star chefs and attracting over 2,000 attendees. Although many of Edgartown’s restaurants are closed during the off-season, a select few await guests with a warm atmosphere year-round. Edgartown Diner is one example, a retro, 60s-style cafe located on Main Street. In the summer, it is not uncommon to find residents lounging on one of the several beaches in Edgartown, including Lighthouse Beach, home to the historic Edgartown Harbor Lighthouse, and East Beach, a beach popular for surfers and fishers.
Lexington
Founded in 1642, the town of Lexington is deeply connected by its Revolutionary War heritage, a history proudly preserved and shared by its community. To fully appreciate Lexington’s past, travelers can join one of the tours led by its knowledgeable residents, who bring the town's stories to life. The Liberty Ride Trolley Tour, guided by an expert in 18th-century attire, explores the Battles of Lexington and Concord, while the Battle Green Tour offers a closer look at the Lexington Battle Green National Historic Landmark.
Each Patriot’s Day, the community gathers on the Battle Green as the Lexington Minute Men reenact the Battle of Lexington, honoring those who fought for the country's independence. Before immersing yourself in Lexington’s history, experience the warmth of the community at local spots like Prince Street Cafe & Bakery, where you can enjoy a bagel, breakfast sandwich, and hot coffee.
Greenfield
Located along the scenic New England Mohawk Trail, the town of Greenfield, home to just under 18,000 residents, remains a warm and welcoming community, even during the cold winter months. The town’s shopping district is the perfect place to spend a chilly Saturday morning, featuring highlights like Whitney Hill Antiques, offering a range of antiques from low to high-end, Federal Street Books, a woman-owned bookstore, and Greenfield Records, a vintage vinyl shop.
The town nurtures its local artists while also hosting nationally recognized performers at venues like the Hawks & Reed Performing Arts Center and the LAVA Center. For artisanal crafts, local farm products, and live music, visit the community’s Farmers Market, held every Saturday from April through October, with occasional winter markets at the Greenfield Public Library.
Provincetown
Provincetown, home to the country’s oldest continuously operating art colony, offers a close-knit art scene that invites visitors to tap into their inner artists. Throughout the year, the Provincetown Art Association and Museum hosts workshops and studio nights in which participants can learn from experienced artists and create art of their own. The colony puts on art events throughout the year as well, such as the 24-Hour Play Festival, which challenges playwrights, directors, and actors to create a production in just 24 hours.
The beaches are another important part of Provincetown’s community, with artists and residents often enjoying the sunshine and beauty of the beaches along the Cape Cod National Seashore Park.
Oak Bluffs
Gingerbread cottages, harbor-side bars, and alpaca farms are a few attractions that make Oak Bluffs one of the most vibrant communities of Martha’s Vineyard. As a national landmark, the Martha's Vineyard Camp Meeting Association is home to these iconic gingerbread cottages, spread across 34 acres, with some dating back to the 19th century and showcasing Carpenter Gothic style.
On sunny weekends, residents flock to Oak Bluffs Harbor, where waterfront restaurants and bars, along with watersports and fishing charters, offer an exciting way to spend the afternoon. Perhaps one of the most interesting parts of Oak Bluff’s agricultural community is the Island Alpaca Farm, where visitors can meet a herd of 50 colorful alpacas.
Wellfleet
The small community of Wellfleet, with a population of around 3,500, provides an authentic experience of Cape Cod’s friendly coastal lifestyle. Upon arriving in town, visitors will be greeted by a number of cute, local shops, such as Moby’s Cargo, a gift shop, Ragg Time, a women’s apparel store, and Jewelry Studio of Wellfleet, a handmade jewelry shop. There are plenty of welcoming inns for an overnight stay, such as Cove Woods Bed and Breakfast, which is just a two-minute walk from the harbor and offers beautiful wooded views from the rooms.
The best way to explore the harbor is with one of Wellfleet’s experienced locals, so consider signing up for a Sailing Charter with Captain Curley or a sunset cruise with Cape Cod Catamaran Sailing Charters.
Fitchburg
Located in northern Massachusetts, Fitchburg has several theaters, museums, and galleries that celebrate local artists and foster a strong sense of community. New Players Guild, for example, is a community theater group that encourages residents of all ages to become active in the theater scene, putting on occasional shows for the public. The Stratton Players is another significant group, as one of the oldest community theater groups in the entire country.
Those wanting to enjoy some New England art can spend an afternoon at the Fitchburg Art Museum or stroll through the Boulder Art Gallery for period and contemporary art pieces. Regarding the outdoors, one of the most popular parks in town is the Crocker Conservation Area, spanning 150 acres and containing forested land and a reservoir.
Falmouth
With its eight cozy villages, 68 miles of shoreline, and numerous white sand beaches, Falmouth is one of Cape Cod’s most beloved and welcoming communities, enriched by a lasting legacy of Portuguese farmers and fishermen. The Nobska Lighthouse is one of the most long-lasting structures in the community. It was constructed in 1828 and protects the boats that pass through the Vineyard Sound and Buzzards Bay.
Those wanting to learn about Falmouth farm life can visit Coonamessett Farm, which allows visitors to pick their own crops, browse farm stands, and enjoy lunch under a shady pavilion. Cape Cod Winery, a popular spot for both residents and visitors, has been part of the community since 1994, using European grape varieties carefully selected to thrive in the local soil.
Not only are these eight towns rich in natural attractions, but their communities are filled with theaters, local shops, and parks that bring people together, even during the coldest months of the year. Whether you are coming from Boston or a smaller Massachusetts town, traveling alone or with family and friends, you will find the warmth and friendliness you have been looking for, as these towns will welcome you like one of their own.
