11 Must-Visit Small Towns in Massachusetts

The most populous state in the New England region of the American Northeast, the Commonwealth of Massachusetts is bounded by the Atlantic Ocean in the east and southeast, the states of Connecticut and Rhode Island in the south, New York in the west, and New Hampshire and Vermont in the north. Christened after the indigenous Massachusett tribe, Massachusetts is unique among all the 50 US States as its rich history and culture predate and exemplify the experiences of the nation as a whole. For adventurists willing to tour a little more than the bustling metropolises of Boston, Springfield, Cambridge, and Worcester, countless small towns scattered across the Bay State are worth exploring. These tiny communities with outstanding natural beauty, historical landmarks, and colorful celebrations, are ideal locales to vacay at any time of the year.


A street lined with boutique eateries in Stockbridge, Massachusetts.
A street lined with boutique eateries in Stockbridge, Massachusetts.

Initially settled in 1734 by British missionaries as a praying town for the indigenous Stockbridge Indians, Stockbridge is located in the Berkshire Hills of Western Massachusetts, along the Housatonic River, about 12 miles south of Pittsfield. Named after the town of Stockbridge in Hampshire, England, this Berkshire County town is best known as an ‘art colony’ and home to renowned American painter Norman Perceval Rockwell and noted sculptor Daniel Chester French. Stockbridge welcomes visitors to stroll down its colorful Main Street and browse the countless specialty shops, art galleries, boutique stores, eateries, and Gilded Age mansions. Some of Stockbridge’s principal sites of interest include the Norman Rockwell Museum, Berkshire Botanical Garden, Naumkeag Mansion & Gardens, Merwin House, Lenox Station Museum, Chesterwood – home & studio of Daniel Chester French, Mission House, National Shrine of The Divine Mercy, Red Lion Inn, and Lake Mahkeenac (Stockbridge Bowl). The merrymakers can witness a show by the Berkshire Theatre Group, or explore the three recreational trails: the Mary V. Flynn Trail, Laura’s Tower Trail, and Ice Glen Trail.


Streetview in Northampton, Massachusetts
Streetview in Northampton, Massachusetts

Hampshire County’s seat, Northampton is situated on the Connecticut River’s western side in Western Massachusetts’s Pioneer Valley, approximately 19 miles north of Springfield. Dubbed “Paradise City,” this quintessential New England town is considered a mecca for artists, musicians, academics, and authors. The town’s burgeoning arts scene and a distinctive bohemian vibe allures thousands of vacationers to Northampton. As the town occupies the heart of the Five-College Area, much of the activities are centered around Smith College – a top-ranked private liberal arts women’s college that has a Museum of Art and an attractive botanic garden. When in town, do visit the significant historic properties from the mid-19th to early 20th century in the Elm Street/Round Hill Historic District, the many bookstores, breweries, recreational parks like the Frank Newhall Look Memorial Park and Childs Park, Northampton farmer markets, Academy of Music Theatre – the country’s sole municipally-owned theater, and the Thornes Marketplace in Downtown. Every year, Northampton hosts the Three County Fair, Northampton Independent Film Festival, LGBT Pride, and an annual Springfest celebration.


Main Street in historic town center of Concord, Massachusetts
Main Street in historic town center of Concord, Massachusetts

Situated close to where the meeting of the Assabet and Sudbury rivers forms the Concord River, this charming Middlesex County town is about 20 miles northwest of Boston. Concord’s fascinating historical landmarks and tranquil surroundings reflect its importance as the site of the Battles of Lexington and Concord that eventually led to the beginning of the American Revolutionary War. History buffs must not miss the Minute Man National Historical Park, Louisa May Alcott’s Orchard House, the Old Manse, Concord Museum, the Walden Pond State Reservation, Sleepy Hollow Cemetery, Wheeler-Minot Farmhouse, and the Old North Bridge. Outdoorsy types can discover the miles of wooded hiking trails in the Great Meadows National Wildlife Refuge, or browse the one-of-a-kind shops and fine restaurants in Concord’s walkable downtown.


Glass Museum in Sandwich, Massachusetts Wikimedia Commons
Glass Museum in Sandwich, Massachusetts Wikimedia Commons

Cape Cod’s oldest town settled in 1637 by a group of settlers from Saugus, Sandwich is located along Cape Cod Bay in Southeastern Massachusetts’s Barnstable County, immediately east of Bourne. Christened after the town of Sandwich in Kent, England, this historic town is renowned for its colonial architecture and six impeccably clean beaches along the bay’s shores. Sandwich’s noteworthy attractions include the Heritage Museums & Gardens, Sandwich Glass Museum, Hoxie House, Wing Fort House, Dexter Grist Mill, Green Briar Nature Center & Jam Kitchen, Sandwich Friends (Quaker) Meetinghouse, and Cape Cod Canal Visitor Center. Additionally, nature enthusiasts can spend quality time at the Shawme-Crowell State Forest and Scusset Beach State Reserve, or head to the 1,350-foot-long Sandwich boardwalk that offers summer seaside fun along with sweeping views of the beautiful marshes and Cape Cod Bay.


A stage wagon ride for visitors in Sturbridge.
A stage wagon ride for visitors in Sturbridge. Editorial credit: Jeff Schultes / Shutterstock.com

Sturbridge, sits along the Quinebaug River in south-central Massachusetts’s Worcester County, approximately 16 miles southwest of Worcester, and 29 miles east of Springfield. The town’s most popular attraction is the Old Sturbridge Village – New England’s biggest living museum, spread over 200 acres and comprising 59 antique buildings, a working farm, and three water-powered mills. For those who wish to experience firsthand what life was like in 18th and 19th-century New England, Old Sturbridge Village is a must-visit. Apart from Old Sturbridge Village, the town’s other interesting sites such as the Tantiusques Reservation, the Wells State Park, Westville Recreation Area, Hyland Orchard & Brewery, and Sturbridge Flea Market also draw many visitors.


Historic buildings at State Street in downtown Newburyport, Massachusetts
Historic buildings at State Street in downtown Newburyport, Massachusetts, via Wangkun Jia / Shutterstock.com

A coastal town in Northeastern Massachusetts’s Essex County, Newburyport is situated close to the mouth of the Merrimack River, around 37 miles north-northeast of Boston. Renowned for its old-time charm, Newburyport captivates visitors with breathtaking views of the Atlantic and a wealth of recreational activities for residents and travelers throughout the year. The town’s downtown shopping district caters to visitors of all ages with many local businesses and eating joints dotting the Market Square. Numerous Federal-style mansions stand as a reminder of the town’s mercantile heritage, besides other tourist magnets such as the Cushing House Museum & Garden, Custom House Maritime Museum, Old South Presbyterian Church, Newburyport Chain Bridge, Maudslay State Park, and the neighboring Parker River National Wildlife Refuge. Newburyport hosts a variety of annual events like Yankee Homecoming, Newburyport Literary Festival, Newburyport Chamber Music Festival, and Waterfront Concert Series.  


Beautiful Stage Harbor in Chatham, Massachusetts
Beautiful Stage Harbor in Chatham, Massachusetts

Occupying the southeastern corner or the “elbow” of Cape Cod in Barnstable County, Chatham is located about 35 miles south of Provincetown and 85 miles southeast of Boston. Initially a shipping, fishing, and whaling center, Chatham has over the years gradually developed into a well-known summer resort town, charming sightseers with its untouched beaches, miles of saline inlets, tidal shoals, barrier islands, fleeting sandbars, and white steeple churches. The town is a reputed shopping destination having a range of clothing boutiques, gift shops, independent bookstores, art galleries, inns, and top-notch restaurants along its winding Main Street. The Atwood House Museum, Chatham Railroad Museum, Chatham Marconi Maritime Center, Chatham Orpheum Theater, Monomoy Natural Wildlife Refuge, Chatham Fish Pier, Stage Harbor Light, Chatham Lighthouse, and Shark Center are some of the town’s must-visit attractions.

Oak Bluffs

Historic gingerbread houses in Oak Bluffs on Martha's Vineyard, Massachusetts.
Historic gingerbread houses in Oak Bluffs on Martha’s Vineyard, Massachusetts.

An idyllic town on Martha’s Vineyard Island in Massachusetts’s Dukes County, Oak Bluffs has historically been a major hub of African-American culture. Serving as one of the focal arriving points for summer visitors, the town is celebrated for its iconic “gingerbread cottages,” and other meticulously maintained mid-to-late 19th century buildings. Beach-goers can easily access the four public beaches: Eastville Beach, Oak Bluffs Town Beach (The Inkwell), Hart Haven Beach, and Joseph Sylvia State Beach; while Oak Bluffs’ harbor serves as a home port for fishing boats and fascinates thousands of recreational boaters all year-round. Walk down Circuit Avenue – Oak Bluffs’ Main Street, and browse the array of small businesses, take a fun ride on the Flying Horses Carousel, visit East Chop Lighthouse, catch a movie at Strand Theatre, play a round of golf at Farm Neck Golf Club, and enjoy the outdoors at Ocean Park.


Quaint shops on a sunny day in Rockport.
Quaint shops on a sunny day in Rockport. Image credit Richard Cavalleri via Shutterstock.

This primarily residential seaside community sits on the edge of Cape Ann Peninsula in Essex County, around 40 miles northeast of Boston, and 20 miles east-northeast of Salem. Boasting several miles of soft sand beaches, historic lighthouses, fishing shacks, and serene walking trails through coastal forests, Rockport is the perfect place to unwind away from the noise of busy cities. The town’s historic Main Street stretching from Dock Square to Beach Street is a state-designated Cultural District packed with locally-owned gift shops, clothing boutiques, candy stores, art galleries, and diners. Some of the leading sites of interest include the Halibut Point State Park & Halibut Point Reservation, Bearskin Neck, Motif No. 1 – Rockport’s most photographed building, Paper House Museum, Shalin Liu Performance Center, Rockport Art Association & Museum, Front Beach, and the adjacent Thacher Island. Every year, Rockport hosts Motif #1 Day, Cape Ann Artisans Spring Tour and Fall Tour, Illuminations Weekend, and the Harvest Fest.


Bradford Street, in Provincetown, Cape Cod, Massachusetts
Bradford Street, in Provincetown, Cape Cod, Massachusetts

Nicknamed, “P-town,” this tiny coastal resort town is placed on the outermost tip of Cape Cod in Eastern Massachusetts’s Barnstable County. Encircled by the Cape Cod National Seashore, this favored summer retreat captivates holidaymakers with its stunning beaches, rich maritime history, exciting nightlife, and trendy tourist ambiance. Ever since the opening of the Cape Cod School of Art by Charles Hawthorne, the town has nurtured artists from all over the globe, earning Provincetown the distinction of being the nation’s oldest continuous art colony. Provincetown’s thriving Commercial Street features multiple art galleries, museums, performance venues, souvenir shops, cool boutiques, inns, and restaurants. Also, do not miss the town’s most recognizable landmark – the Pilgrim Monument, and participate in various annual events like First Light Provincetown, Provincetown PRIDE, Provincetown International Film Festival, Provincetown Portuguese Festival, and Provincetown Jazz Festival.  


Uncle Tim's Bridge in Wellfleet, Cape Cod, Massachusetts.
Uncle Tim’s Bridge in Wellfleet, Cape Cod, Massachusetts.

Famed for its plentiful oysters, this enchanting beach town in Barnstable County occupies the northeastern arm of Cape Cod, roughly 12 miles south-southeast of Provincetown. Bounded by the Atlantic Ocean in the east and Cape Cod Bay in the west, about 70% of Wellfleet’s land area is protected as a part of the Cape Cod National Seashore. Home to 3,566 year-round residents, the town’s population swells sixfold during the warmer months, when vacationers visit in large numbers to enjoy the miles of clean sandy beaches, spring-fed ponds, fine art galleries, great seafood restaurants, and the magnificent Wellfleet Harbor. Spend some time at the Mass Audubon Wellfleet Bay Wildlife Sanctuary, Wellfleet Flea Market, Marconi Wireless Station, and Wellfleet Historical Society & Museum; hike the Great Island Trail and Cape Cod Rail Trail; and take part in the annual October Wellfleet OysterFest.

From the laid-back seaside towns of Cape Cod to the historic mountain towns, the innumerable small towns in the nation’s 6th smallest and 16th most populous state have something for everyone. Whether you are a heritage buff, a passionate hiker, a cultural enthusiast, a seafood lover, or someone who loves adventures, you must tour these lovely small towns in the Pilgrim State.

Get Insightful, Cutting-Edge Content Daily - Join "The Neo Jim Crow" Newsletter!

We don’t spam! Read our privacy policy for more info.

Get Insightful, Cutting-Edge, Black Content Daily - Join "The Neo Jim Crow" Newsletter!

We don’t spam! Read our [link]privacy policy[/link] for more info.

Get Insightful, Cutting-Edge, Black Content Daily - Join "The Neo Jim Crow" Newsletter!

We don’t spam! Read our [link]privacy policy[/link] for more info.

This post was originally published on this site