11 Most Underrated Towns in Massachusetts

The Commonwealth of Massachusetts, the United States’s 6^th smallest and 16^th most populous state, is bounded by the expansive Atlantic Ocean to the east and southeast and the abutting states of Connecticut, Rhode Island, Vermont, New Hampshire, and New York. Placed in the New England region of the American Northeast, Massachusetts is a historically and culturally rich state among all the 50 US States. Although holidayers mostly prefer to tour the state’s bustling metropolises like Springfield, Worcester, Cambridge, and the state capital, Boston, rather than the state’s tiny communities, the uncountable small towns speckled all over Massachusetts’s 7,800 sq. mi (land) terrain should not be overlooked. So, what are you waiting for? Pack your bags and embark on a journey to these underrated Bay State towns for a memorable vacation with your dear ones.

Chatham

Occupying Cape Cod’s southeastern corner (“the elbow”), this Barnstable County town is situated approximately 35 miles south of Provincetown, 20 miles east of Barnstable, and 85 miles southeast of Boston. Initially called “Monomoit” and founded as a fishing, shipping, and whaling hub, Chatham has gradually developed over the years into a leading summer resort town, captivating travelers with its pristine beaches, fleeting sandbars, barrier islands, tidal shoals, coves, miles of saline channels, and iconic white steeple churches. Chatham’s dynamic Main Street is jam-packed with various high-end clothing boutiques, independent bookstores, gift shops, art galleries, hotels, and excellent eateries. The Commercial Fishing Pier, Atwood House Museum, Shark Center, Chatham Railroad Museum, Stage Harbor Light, Chatham Marconi Maritime Center, Monomoy Natural Wildlife Refuge, Chatham Lighthouse, and Chatham Orpheum Theater are some noteworthy attractions.

Wellfleet

A charming beach town, Wellfleet is located midway between Cape Cod’s “tip” and “elbow” in Barnstable County, about 12 miles south-southeast of Provincetown. Famous for its abundant supply of oysters and abutted by the Atlantic Ocean and Cape Cod Bay, around 70% of the community’s land area is protected as a part of the Cape Cod National Seashore. Home to 3,566 residents all year round, Wellfleet’s population surges sixfold, with thousands of vacationers flocking to this beachside getaway during the warm season. Spend time at the awe-inspiring Wellfleet Harbor, unwind along the spring-fed ponds and the spotless beaches, peruse the fine art galleries, and grab tasty meals at the seafood restaurants. Also, check out the Wellfleet Flea Market, Wellfleet Historical Society & Museum, Mass Audubon Wellfleet Bay Wildlife Sanctuary, and Marconi Wireless Station; participate in the Wellfleet OysterFest each fall, and trek the Cape Cod Rail Trail bike path and the Great Island Trail.

Concord

Concord, an adorable town in Eastern Massachusetts’ Middlesex County, is situated close to where the confluence of Assabet and Sudbury rivers form the Concord River, around 20 miles northwest of Boston. The plethora of interesting historical properties and peaceful settings reflect the town’s importance as the location of the Battles of Lexington and Concord, which finally led to the commencement of the American Revolutionary War. The Minute Man National Historical Park, Old Manse, Walden Pond State Reservation, Wheeler-Minot Farmhouse, Old North Bridge, Louisa May Alcott’s Orchard House, Concord Museum, and Sleepy Hollow Cemetery are must-visits for all heritage buffs. Outdoor enthusiasts should traverse the several miles of hiking trails at the Great Meadows National Wildlife Refuge, window-shop at the eclectic shops, and taste mouthwatering dishes at the award-winning diners in Concord’s strollable downtown.

Newburyport

Acclaimed for its old-time appeal, this coastal hamlet in Essex County of Northeastern Massachusetts is located on the southern shores of the Merrimack River, where it empties into the Atlantic Ocean, approx. 37 miles north-northeast of the state capital. Newburyport lures sightseers with astounding views of the mighty Atlantic and a multitude of recreations for both residents as well as visitors all year round. With several locally-owned businesses and dining places in the Market Square, Newburyport’s Downtown Shopping District cater to tourists of all ages. Furthermore, the particular points of interest such as the Cushing House Museum & Garden, Old South Presbyterian Church, Maudslay State Park, Custom House Maritime Museum, Newburyport Chain Bridge, and the adjacent Parker River National Wildlife Refuge; and plenty of Federal-style buildings line the streets of the town. Varied celebrations like the Newburyport Literary Festival, Waterfront Concert Series, Yankee Homecoming, and Newburyport Chamber Music Festival are held every year.

Oak Bluffs

The principal mecca of African-American culture, Oak Bluffs is a quaint town located on Martha’s Vineyard in Massachusetts’s Dukes County. Besides being one of the main arrival points for summer visitors, Oak Bluffs is widely known for its typical gingerbread cottages and carefully restored mid-to-late 19th-century properties. The four public beaches, Joseph Sylvia State Beach, Oak Bluffs Town Beach (The Inkwell), Eastville Beach, and Hart Haven Beach, can be easily accessed by coastal vacationers, whereas Oak Bluffs’ harbor is an ideal homeport that draws recreational boaters throughout the year. Have a look at the wealth of small businesses in Circuit Avenue – the Main Street, play golf at Farm Neck Golf Club, visit the East Chop Lighthouse and soak in the town’s beauty at Ocean Park, join in for a fun ride on the Flying Horses Carousel and watch a movie at the Strand Theatre.

Sturbridge

This picture-perfect town is situated along the Quinebaug River in Worcester County of south-central Massachusetts, about 16 miles southwest of Worcester. The Old Sturbridge Village, considered the most expansive living museum in New England, is spread over 200 acres and comprises a working farm, three water-powered mills, and 59 antique buildings. For those who wish to know what daily life was like in the region during the 18^th and 19^th centuries, a trip to Old Sturbridge Village is a must. In addition to the Old Sturbridge Village, Sturbridge's other places of interest include the Tantiusques Reservation, Hyland Orchard & Brewery, Wells State Park, Sturbridge Flea Market, and Westville Recreation Area.

Northampton

Northampton is a quintessential New England town in Western Massachusetts’s wooded Pioneer Valley on the western side of the Connecticut River, about 19 miles north of Springfield. Called “Paradise City,” this seat of government of Hampshire County oozes a peculiar bohemian vibe and is regarded as a meeting place for thousands of academicians, writers, artists, and musicians. Occupying the heart of a Five-College Area, many of the town’s activities take place around the prestigious all-women’s Smith College, which houses an aesthetic botanic garden and a Museum of Art. Tourists visiting Northampton must not miss the remarkable mid-19^th to early 20th-century structures in the Round Hill Historic District, the Thornes Marketplace, Northampton Farmer Markets, outdoor parks like the Childs Park and the Frank Newhall Look Memorial Park, Academy of Music Theatre, and the numerous breweries, and bookstores in the Downtown. Northampton hosts an array of yearly events like a Springfest celebration, the Northampton Independent Film Festival, LGBT Pride, and the Three County Fair.

Provincetown

Surrounded by the Cape Cod National Seashore, this teeny coastal hamlet, often called “P-town,” occupies the northernmost edge of Cape Cod in Barnstable County of Eastern Massachusetts. Boasting stunning soft sand beaches, fascinating maritime heritage, electrifying nightlife, and a welcoming atmosphere, Provincetown entices vacationers worldwide. Besides, the town has earned the distinction of being the oldest continuous art colony in the country and has supported countless art aficionados for eons. The vibrant Commercial Street of this LGBT+-friendly destination has scores of art galleries, souvenir shops, museums, cool boutiques, entertainment venues, cozy inns, and diners. Additionally, check out the Pilgrim Monument – Provincetown’s most conspicuous landmark, and partake in the town’s many annual festivals.

Sandwich

Initially inhabited by the indigenous Wampanoag tribe before being colonized by a team of settlers from Saugus in 1637, Sandwich is Cape Cod’s oldest settlement, located just east of Bourne along Cape Cod Bay in Barnstable County. Dubbed after Sandwich, England, this historic town is famous for its well-preserved colonial properties and six clean beaches along the shores of the bay. Sandwich’s exciting sites include the Heritage Museums & Gardens, Hoxie House, Dexter Grist Mill, Sandwich Friends (Quaker) Meetinghouse, Sandwich Glass Museum, Wing Fort House, Cape Cod Canal Visitor Center, Green Briar Nature Center & Jam Kitchen. Furthermore, outdoorsy types can explore the Scusset Beach State Reserve and Shawme-Crowell State Forest or visit the Sandwich boardwalk to enjoy unparalleled views of Cape Cod Bay.

Rockport

Rockport, a seaside community in Massachusetts’ Essex County, sits on the extremity of Cape Ann Peninsula, roughly 20 miles east-northeast of Salem and 40 miles northeast of Boston. With miles and miles of sandy beaches, walking trails through coastal forests, fishing shacks, and ancient lighthouses, this tourist town is ideal for those who wish to relax and unwind. Extending from Dock Square to Beach Street, Rockport’s classic Main Street – a state-designated Cultural District has gift shops, fashion boutiques, art galleries, candy stores, and eateries. Paper House Museum, Rockport Art Association & Museum, Halibut Point State Park & Halibut Point Reservation, Shalin Liu Performance Center, Bearskin Neck, Front Beach, and Motif No. 1 are the town’s prominent attractions. Annually, Rockport hosts various events like the Harvest Fest, Motif #1 Day, Illuminations Weekend, and Cape Ann Artisans Spring & Fall tours.

Stockbridge

Christened after its namesake English town, Stockbridge, located in Western Massachusetts’ Berkshire County, was first settled as a praying town for the native Stockbridge Indians by British missionaries in 1734. This scenic town in the Berkshire Mountains along the Housatonic River is famed as an ‘art colony’ and for being the hometown of Norman Perceval Rockwell, the distinguished American painter, and Daniel Chester French, a renowned sculptor. Tourists are welcome to walk down the town’s lively Main Street and browse the umpteen Gilded Age structures, boutique stores, art galleries, specialty shops, and restaurants. Stockbridge’s exciting sites include the Norman Rockwell Museum, Naumkeag Mansion & Gardens, National Shrine of The Divine Mercy, Lenox Station Museum, Red Lion Inn, Mission House, Berkshire Botanical Garden, Chesterwood – the studio & residence of Daniel Chester French, and Lake Mahkeenac (Stockbridge Bowl). Revelers can traverse the three recreational trails: the Ice Glen Trail, Mary V. Flynn Trail, and Laura’s Tower Trail, or catch a show by the Berkshire Theatre Group.

Discover Massachusetts Beyond The Cities

From the pretty Cape Cod town of Chatham to the gorgeous mountain town of Stockbridge, the innumerable towns in the Commonwealth of Massachusetts have something for every tourist. With incredible natural wonders, lively celebrations, enthralling attractions, and many recreational activities, the underrated towns in the Pilgrim State are worth visiting.