8 Massachusetts Small Towns With Unmatched Friendliness
New England states possess a distinct and unmatched vibe. They are a dazzling blend of rich history, sophistication, and a pristine landscape. From the blooms of spring to the snowy stillness of winter, each season paints the region with picture-perfect views. Many small towns in Massachusetts add warmth to the state. Westport offers a quiet rural retreat, and Great Barrington is the spot to eat, drink, and live it up. Spend a week in Newburyport for the timeless Yankee Homecoming Festival, or head to Concord to take a deep dive into the American Revolution. Any road traveled in Massachusetts leads to noteworthy experiences, friendly faces, and a warm welcome.
Newburyport
Newburyport is an old-timey town with kind neighbors along the banks of the Merrimack River. Visit in the summertime for the energetic Yankee Homecoming. This weeklong event commemorates the town's history and has brought the locals together since 1958. Browse the marketplace, get rowdy at the road rally, or partake in a heritage tour or waterfront workout session. Book lovers can celebrate the love of written works at the Newburyport Literary Festival. The weekend affair is the perfect addition to the blossoming of springtime in Massachusetts. Previous activities include a delicious breakfast with poetry readings, The Ins and Outs of Indie Publishing, and presentations featuring fiction and nonfiction texts.
Settled in 1635 and becoming separate from Newbury in 1764, the town is brimming with history. Walk through multiple galleries at the Custom House Maritime Museum for a closer look at Newburyport's coastal heritage. From time to time, the museum hosts events such as exhibition openings and First Friday Lectures. Bring the kids to the Children's Discovery Center for a family-friendly venture. After a thrilling day, rest up at the historic Essex Street Inn. Visitors love the convenient downtown location and comfortable rooms.
Greenfield
Embrace the great outdoors in Greenfield, a city surrounded by natural beauty. Spend some time at Rocky Mountain Park, home to the striking Poet's Seat Tower. Climb up the tower to see breathtaking panoramic views of Greenfield and beyond. Watch the sunset or photograph the magazine-worthy fall foliage from way up high. Located just a short drive away, hit the trails by foot or mountain bike at Mount Sugarloaf State Reservation. Trek to the summit and bask in the endless vista of the Connecticut River Valley.
Mingle and be merry with Greenfield residents at one of the town's lively events. Kick off the sunny warmth of June with the Green River Festival. Dance away to the live music from Friday until Sunday. Bring the kids for the CactusHead Puppets, Tanglewood Marionettes, and special kid-centered music. Nothing beats a good old-fashioned county fair. From agricultural shows, midway rides, and a parade, the Franklin County Fair is a fun-spirited summer extravaganza. Stay until late summer for the Annual Harvest Supper. Bring a plate and utensils, and have the feast of a lifetime.
Great Barrington
Try new flavors as diverse dining runs rampant in Great Barrington. Support local craftsmanship at Barrington Brewery & Restaurant, offering handcrafted beers brewed on-site. From Raspberry Ale to Barrington Brown, there is a little something for every taste. For dinner, head to Cafe Adam for locally sourced fine dining. The seasonal menu changes frequently and offers an eclectic blend of cuisines.
Great Barrington is also an artsy little Massachusetts town bursting with creative feats. Gather with the rest of the art lovers at the Berkshires Arts Festival. With art demonstrations, workshops, food, and wine, the three-day exhibition is a first-class experience. Browse masterpieces from more than 150 artists, from ceramics to sculptures, painting, mixed media, and metalwork. Take home a piece of Massachusetts at the GB Arts Market. From jewelry to candles and hats, everything is handmade by local and regional residents.
Westport
Perfectly placed right along the Rhode Island border, Westport is a quiet farming town. The rural retreat is a hotspot for purchasing succulent produce and seeing all the happy animals. Pop by the Westport Farmers' Market or Alderbrook Farm for fresh, locally grown produce, and use it in a homemade culinary creation. Those who are not crafty in the kitchen can purchase freshly prepared foods at Saugatuck Provisions. Beautify any space with stunning flowers from Paradise Hill Farm, or pick up a jar of honey, maple syrup, or jam for a yummy souvenir.
From vibrant fall foliage to endless pumpkin patches, New England is a quintessential fall destination. Celebrate this enchanting season at The South Coast Harvest Festival. Past highlights include pumpkin painting, a tractor showcase, musical performances, a dog show, apple vendors, and fall-themed displays. Grab a ticket for Sunset Music at Westport Rivers Vineyard & Winery from June to September. Light up Friday nights with live music from 6 pm until 8 pm. Make a toast with a glass of wine while watching the sunset and appreciating the calming atmosphere.
Marion
Marion is a hidden treasure in Massachusetts, and the town is a prime example of a refined and authentic slice of coastal New England. As a proud owner of one of the largest sailing fleets in the state, many visitors flock to Marion in search of its maritime culture. Take a journey to the Sippican Harbor to see the Bird Island Lighthouse. Both historical and a sight to behold, the lighthouse has been a notable Marion landmark for over 200 years. For an in-depth look at marine life, science, and the environment, view the exhibits at the Marion Natural History Museum. You will get lost in the magical collections, from waterfowl and butterfly exhibits to Native American artifacts.
Get to know the town's people at one of Marion's bustling events. Head to the Marion Art Center in October for the Halloween Parade. Open to all ages, see a range of costumes from adorable kids to creative adults. In December, watch Santa arrive by boat at the Marion Village Christmas Stroll. Watch the tree light up at Bicentennial Park and cozy up with cookies and eggnog at this heartwarming gathering.
Concord
Twenty miles west of Boston lies the postcard-worthy town of Concord. Known for its ties to the American Revolution, this idyllic town holds an alluring charm. Take a moment to imagine history unfolding at the Minute Man National Historical Park. Stroll past the legendary battle site by walking on the Battle Road Trail. Make a stop at the Minute Man Visitor Center and watch the multimedia presentation. The production runs for almost 30 minutes and helps visitors get a feel for what happened on April 19, 1775. Pay respects to the fallen soldiers at the Old Hill Burying Ground in Monument Square. The gravesite contains remains and marked headstones of early war veterans. Visitors in the area on April 19 can capture the Patriots Day Parade, featuring over 50 parade units.
Make some new friends at one of Concord's many festivities. Verrill Farm truly embodies the spirit of friendly neighborhood farmers. The massive 200-acre property has been family-owned for over 100 years. Join in on the fun at a fermentation class, strawberry cocktail party, asparagus tour, or Mother's Day Brunch. And nothing beats a good read: celebrate passionate writers from all over at the Concord Festival of Authors in the fall.
Sudbury
As with many Massachusetts cities and towns, colonial roots run strong in Sudbury. Step back in time by staying at The Wayside Inn, a masterpiece built in 1716. With only 10 rooms furnished with vintage items, it is an exclusive experience not to be missed. Take some pictures of the iconic Wayside Inn Grist Mill. Whether decked in snow or shining bright with fall leaves, this storybook mill always makes the best photo opportunity. The Redstone School House is another Sudbury treasure not to be missed. This adorable one-room structure is well-preserved and rumored to be the inspiration for the famous nursery rhyme "Mary Had A Little Lamb".
Feel right at home in Sudbury's warming ambiance and partake in local excitement. The town is patriotic and proud, as evidenced by its colossal 4th of July Parade, an hour-and-a-half parade featuring 16 different musical performances, firetrucks, old vehicles, and agricultural displays. Wear red, white, and blue, and show your spirit at this dynamic celebration. When sweater weather arrives, it is time for the Meadow Walk Fall Festival. Satisfy cravings with the food samples, create a work of art at the pumpkin painting, and let the kids loose at the bounce house.
Northampton
Northampton is a cultural college town bursting with character and bohemian flair. Learn to live in the moment and cherish the surrounding beauty at the Botanic Garden of Smith College. Breathe in the fresh air while wandering through the six acres of manicured outdoor gardens. Identify plants from all around the world at the Lyman Plant House & Conservatory. With rooms tailored to specific climates, the space allows thousands of plants to thrive. Spot everything from tropicals to fall mums, orchids, and even aquatic plants. After an otherworldly experience in the plant world, head to Familiars Coffee & Tea to continue the rejuvenation process. Dig into handcrafted food and beverages that are locally sourced and made with love.
History meets genuine hospitality at the Three County Fair, the oldest ongoing agricultural fair in the nation. The fair features animals galore, from dairy cows to horses, sheep, rabbits, and oxen. Stick around for the legendary apple pie contest, kiddie tractor pull, and classic car show. Finally, a town as imaginative as Northampton naturally has a buzz-worthy art scene. Show support at the Paradise City Arts Festival in May, where works range from art glass to ceramics, furniture, and fashion designs, all crafted by residents.
Friendly Smiles Await in Massachusetts
Massachusetts boasts many close-knit towns teeming with exhilarating attractions and busy event calendars. Relish in the good life with live music at the Green River Festival in Greenfield. Take a trip to Marion, a secluded prize with those quintessential coastal New England vibes. Relive history with a stay at the historical Essex Street Inn in Newburyport while attending the Newburyport Literary Festival. From meeting new connections at Verrill Farm in Concord to patriotic cheers at Sudbury’s 4th of July Parade, Massachusetts always leaves visitors smiling and having the best time.
