9 Eclectic Small Towns In Massachusetts
Admitted to the Union as the 6th State in February’1788, the Commonwealth of Massachusetts set in the New England region of the Northeastern US captures interest with its natural spectacles, historical attractions, and colorful cultures. Although holidayers intending to spend their vacation days in this ‘Bay State’ (so monikered for the umpteen large bays defining the state’s extensive coastline), customarily single out the capital city Boston, and other populous urban hubs, the unnumberable eclectic small towns punctuating the Pilgrim State are worth sojourning to regardless of the time of year.
Rockport
Rockport, a bewitching coastal settlement in Essex County, sits at the Cape Ann peninsula’s eastern extremity, approx. 20 miles east-northeast of Salem. This fewer than 7,000 residents town invites excursionists to gawk in amazement at the miles of white-sand beaches, unruffled hiking trails via coastal forests, fanciful fishing shacks, and archaic lighthouses. Chock-full of gift shops like The Pewter Shop, boutiques like Floating Lotus-Rockport, art galleries like Mercury Gallery, and seafood restaurants like The Fish Shack Bar & Restaurant, Rockport’s Main Street is a state-designated Cultural District offering abundant shopping and dining options all year long. Additional sites of interest such as the Rockport Art Association & Museum, the Halibut Point State Park & Halibut Point Reservation, and the Shalin Liu Performance Center are not to be missed.
Lenox
This teeny Berkshire County town is a favored warm-weather sanctuary set amidst the Berkshire Mountains in Western Massachusetts. Primarily populated by the Indigenous Mahicans and labeled ‘Yokuntown,’ the settlement was later renamed after the British army officer Field Marshal Charles Lennox. Travelers on an excursion to Lenox must drop around to see The Mount - the country house of eminent American writer Edith Wharton, the historical exhibits displayed at the Berkshire Scenic Railway Museum, and the Tanglewood Music Center - the summer house of Boston Symphony Orchestra, accessorily participating in hiking, cross-country skiing, and picnic activities at Kennedy Park.
Chatham
Situated on Cape Cod’s southeastern corner, this delightful Barnstable County town is just 85 miles southeast of the state capital. Established as a fishing, shipping, and whaling mecca, Chatham has over time prospered into a coveted holiday spot spellbinding seasonal holidaymakers with the unspoiled beaches, barrier islands, saline inlets, transient sandbars, and emblematic churches. Chatham’s sinuous Main Street is a fabulous retail area lined by scores of gift shops like Yankee Ingenuity, women's clothing stores like Sundance Clothing, bookstores like Yellow Umbrella Books, and eateries like Pates Restaurant that cater to people of all ages in tandem with other prominent points of interest such as the United States Coast Guard-operated Chatham Lighthouse, Chatham Orpheum Theater, Chatham Marconi Maritime Center, and Monomoy Island National Wildlife Refuge.
Northampton
The administrative center of Western Massachusetts’ Hampshire County, Northampton occupies the tree-laden Pioneer Valley on the Connecticut River’s western side, roughly 19 miles north of Springfield. Styled “The Paradise of America,” this archetypal New England community is a gathering place for wordsmiths, instrumentalists, fine artists, and academics from far and wide. A gamut of town activities take place around the high-ranked Smith College which also has an exquisite botanic garden and a Museum of Art. When in town, do haunt the traditional houses in the Round Hill Historic District, the Frank Newhall Look Memorial Park, and the Thornes Marketplace, plus freeing time to join the Northampton Independent Film Festival and the annual Springfest celebration.
Sturbridge
Home to 9,867 residents as per the 2020 US Census, Sturbridge sits by the side of the Quinebaug River, nearly 16 miles southwest of Worcester in the state’s south-central portion. The praiseworthiest allurement of this Worcester County town is the Old Sturbridge Village - New England’s prodigious living history museum extending over 200 acres and incorporating 59 time-honored buildings, 3 water-powered mills, and an operational farm. Those who wish to acquire knowledge about rustic New England life in the first half of the 19th century gotta stop at the Old Sturbridge Village. Likewise, not to miss are Sturbridge’s discrete tourist spots like the Hyland Orchard & Brewery, Sturbridge Flea Market, and the nearby 1,400-acre Wells State Park.
Concord
Concord, whose town center is located close to where the Sudbury and Assabet Rivers’ confluence form the Concord River, is a winsome Middlesex County town, almost 20 miles northwest of Boston. Deemed a well-to-do suburb of Greater Boston, the blissful milieus and riveting heritage properties adroitly evince Concord’s relevance as the site of the American Revolutionary War’s initial military engagements. Heritage addicts should go straight to the Minute Man National Historical Park, the Sleepy Hollow Cemetery, and the Orchard House of Louisa May Alcott, while the queer Downtown shops and Great Meadows National Wildlife Refuge’s miles of exploration trails enthrall shopaholics and adrenaline junkies respectively.
Stockbridge
Founded by British missionaries in 1734 as a ‘praying town’ for the native Stockbridge-Munsee Community, this Berkshire community sits along the Housatonic River precisely 12 miles south of Pittsfield. Baptized after its namesake English town, Stockbridge, being the home of Daniel Chester French - a distinguished sculptor and master painter Norman Perceval Rockwell, is an acclaimed creative community. Inspect Main Street’s Gilded Age manors, gift shops like Whispered The Heart - Local Artisan gift shop, and restaurants like Main Street Café; crisscross the Mary V. Flynn Trail and Ice Glen Trail; and quickly visit the Norman Rockwell Museum, Chesterwood - Daniel Chester French’s residence & studio, and Naumkeag Mansion & Gardens.
Williamstown
Bay State's northernmost town, sharing a boundary in the west with New York and in the north with Vermont, Williamstown is a photographic college town in Berkshire County. Drawing academicians from across the globe to Williams College’s main campus, Williamstown also attracts the attention of creative connoisseurs thanks to the extensive contemporary artwork housed in the Williams College Museum of Art and the Sterling & Francine Clark Art Institute. Furthermore, learn about the town’s yesteryears at the Williamstown Historical Museum, traverse the 4.5 miles of hiking trails on the 316-acre Field Farm, and savor common New England classics served by The Barn Kitchen & Bar.
Wellfleet
Positioned midway betwixt the ‘tip’ and ‘elbow’ of Cape Cod and bounded by Cape Cod Bay to the west and Atlantic Ocean to the east, Wellfleet is a hypnotic beachside community in Barnstable County, about 12 miles south-southeast of Provincetown. Best known for its plentiful oysters, the town’s population (about 3,566 inhabitants as per the 2020 US Census) increases six times during the warmer months when holidayers throng in massive numbers to take note of the immaculate fine-sand beaches (notably Marconi Beach), numerous spring-fed ponds, art galleries like Left Bank Gallery, gift shops like Newcomb Hollow Shop, restaurants like The Wicked Oyster, and the impressive Wellfleet Harbor. Drop in at the Mass Audubon Wellfleet Bay Wildlife Sanctuary, the Marconi Wireless Station, and the Wellfleet Historical Society & Museum, besides showing up at the yearly two-day Wellfleet Oyster Fest on the weekend after Columbus Day.
From the historic alpine town of Lenox to the enticing seaside town of Wellfleet, the nation’s 16th most populous and 6th smallest state packs a handful of towns within its jurisdiction. Each of these beguiling hamlets with their mind-boggling environs, widely acclaimed historic landmarks, bountiful recreations, finger-licking foodstuffs, and colorful yearly festivities has something for every tripper. So, if you want to experience the best of all that the Puritan State has, head directly to these mesmeric towns and make lasting memories on your trip.
