The entrance of Nantucket, Massachusetts.

13 Best Small Towns In Massachusetts

A state of beaches, witch hunts, centuries of history, and endless charm, Massachusetts is home to many small towns adding their own vibe to the mix. Here is a bucket list full of charisma for one's next holiday to see all best that Massachusetts has to offer.


Newburyport historic downtown including State Street and Market Square with Merrimack River.

The coastal gem in northern Massachusetts comes with a scenic harbor and Newburyport's historic seaport. The town's long history dates back to the Revolutionary War, including when abolitionism (freeing from slavery) became popular, and the town served as an important stop on the Underground Railroad. Set just south of the New Hampshire border, its quaint and walkable downtown and the State Street flaunts a mix of modern and old-fashioned delights, including ice cream parlors and boutique shops. Harbor-side, there are whale-watching tours, oysters and hot lobster rolls at the Sea Level Oyster, and a lovely boardwalk. The hikers will enjoy the scenic trails at the Parker River National Wildlife Refuge.


Gloucester, Cape Ann, Massachusetts
Aerial view of Rocky Neck and Gloucester Harbor in City of Gloucester, Cape Ann, Massachusetts.

Gloucester is perched picturesquely on an outcropping on the northern coast of Massachusetts as a rich-in-sights town known for its fishing harbor, active since the colonial times. Set on the southern shore of Cape Ann, the prevalent activities include harbor sightseeing cruises, schooner sailing, deep-sea fishing, and whale watching, along with several beaches. The enthusiasts of land-based pursuits can enjoy the marine sights while on "foodie" or historical tours through town. Built in 1920 by a notable Inventor John Hays Hammond, the Hammond Castle resembles a medieval castle visible from sea and shore. It comes complete with turrets and flying buttresses and evokes romanticism as a popular venue for weddings, Renaissance festivals, etc. The seaside Sleeper-McCann House, known as Beauport, comprises the former home of interior designer Henry Davis Sleeper. The Cape Ann Museum is great to admire local art and learn about the area's history, while the Maritime Gloucester comes with an aquarium and exhibits on the area's maritime legacy.


Boats are moored in a bay near the Chatham Fish Pier.

The small, adorable town of Chatham is all about the sun-drenched beach worshipped by locals and tourists alike. Chatham Beach comes with the historic Chatham Lighthouse, some of the most pristine coastal spots, and the quaint downtown within hand reach. For a picture-perfect day, one can catch the lazy morning sunrays on the sands, follow with an atmospheric stroll through the town's sprinkling of cute shops and cafes, and land in a top-notch restaurant for a seafood-fest, such as the Impudent Oyster. The Monomoy National Wildlife Refuge, the Shark Center, and the Chatham Railroad Museum comprise beloved family pastimes, while the art fans praise the Steve Lyons Art Gallery and the Atwood Museum.


Concord, Massachusetts
Tourists kayaking on the Concord River at Minute Man National Historic Park near Concord. Editorial credit: Jay Yuan /

Rich in Revolutionary and literary histories, Concord is rife with landmarks from the early days of the Revolutionary War, such as its North Bridge, where, in 1775, the "shot heard 'round the world" was fired. The small town is also intertwined with the lives of the many great American authors, such as Henry David Thoreau, who immortalized the Walden Pond while staying there in solitude. The Emerson House is where Emerson wrote "Self Reliance" and entertained other prominent writers and thinkers, including Thoreau and Louisa May Alcott. Their common final resting place is at the Sleepy Hollow Cemetery, known as the Author's Ridge. The Concord Museum takes one on a journey through period rooms, from the Native American settlements and settlers' arrival to the more recent events, significant sites, and stories on local residents. There is also Thoreau's writing desk and personal items, a re-creation of Ralph Waldo Emerson's study, along with one of the two legendary lights, the Paul Revere lantern that alerted the revolutionaries of the British attack.

Great Barrington

Great barrington
Railroad Street lined with traditional brick buildings and colourful shops and restaurants in Great Barrington.

The incredibly charming town with a name ringing of the beautiful nature around is set in the picturesque valley of the Housatonic River in southwestern Massachusetts. Housing multiple cultural and historic sites, including the Mahaiwe Performing Arts Center, the adorable downtown also comes with one of the area's richest restaurant and retail scenes. Listed by the Smithsonian as the best town in America, Great Barrington is the ideal place to spot nature with breathtaking views of the Taconic Mountains, the Ski butternut, the Housatonic river walk, and Lake Mansfield. The Monument Mountain Reservation offers unforgettably scenic hikes, while the Housatonic Flats Reserve is known for the beautiful Berkshires.


Connecticut river
Connecticut River flowing near Hadley.

Located in Hampshire County, Hadley is small but popular for being set ideally along Route 9. Settled way back in 1659 by Puritans, it was known for witch hunts, including the trial and acquitting of Mary Webster, the wife to the son of one of Hadley's founders. Concentrated with all the charisma that Massachusetts has to offer, Hadley is great for strolling along with some wonderful natural vistas right in town. The popular Skinner State Park with beautiful trails offers the second-to-none views of the Connecticut River Valley and mountain biking and hang gliding. For some one-on-one time with nature, there's hiking at the Silvio O Conte National Fish and Wildlife Refuge, while to disconnect from modern life altogether, the Porter Phelps Huntington House Museum will transport one back in time. There is also the New England Falconry and the Hadley Farm Museum for the animal lovers and kids, while whole families love the Hampshire Mall.


The Mount, home of American author Edith Wharton. Editorial credit: LEE SNIDER PHOTO IMAGES /

An industrial town and then an art colony in the 1800s, the same time that the railroad was found, Lenox quickly became a popular summertime destination, with notable residents including Catharine Sedgwick and Nathaniel Hawthorne. It is home to Shakespeare & Company and Tanglewood, the summer headquarters of the Boston Symphony Orchestra, while its scenic streets brim with fine dining establishments. Nestled in the Berkshires of Western Massachusetts, the town is known amongst the outdoors people for its year-round pursuits. Comprising a lovely autumn scene with vibrant foliage colors, the Pleasant Valley Sanctuary is great for hiking and biking the paths. Many ski resorts open in the area once the temperatures drop. More winsome scenery includes interesting attractions like Edith Wharton's Home, The Mount. 


Beautiful homes of Nantucket, Massachusetts.
Beautiful homes of Nantucket, Massachusetts.

The adorable island town of Nantucket is one of the two most iconic East Coast summer beach getaways. The legendary escape off the coast of Cape Cod is known for the wind-swept dunes, architecturally marvelous cedar-shingled houses, and the "perfectly preppy" atmosphere. The vibrant downtown full of upmarket boutiques, seafood eateries, and historic churches lining the cobblestoned streets that lead to the beaches is hard to come by and forget. In fact, the town is so irresistible that once discovered, it is the place where people want to visit times again for the holidays, blind to all of the other great, albeit more crowded, summertime destinations. 


Set in a rather remote location of the western Massachusetts, Northampton is a true center of cultural activity and rich history, on par with the eastern portion of the state. The downtown area comes with an awesome variety of specialty shops and impressive culinary establishments, rare for small towns. There are also numerous boutiques, galleries, and used book shops for dream-come-true quaint destination activities. The Smith College is a prominent women's liberal arts school enriching the town's artistic and cultural life. The collections at the Smith College Museum of Art includes ancient artwork, pieces from different continents, as well as a special collection focusing on functional art, art after 1950, and works on paper. The Historic Northampton is a museum spreading through three historic homes with changing exhibits of art and historic topics, artifacts from the region's earliest occupants, and permanent exhibits that focus on the town's history. 

Oak Bluffs

Aerial view of Oak Bluffs, Martha’s Vineyard
Aerial view of Oak Bluffs, Martha’s Vineyard.

Set on the idyllic Massachusetts island Martha's Vineyard and named after the oak groves overlooking the Nantucket sound, Oak Bluff is brimful with 19th-century buildings, including cute gingerbread cottages back-dropped by endless water vistas. The Ocean Park Gazebo comprises the best spot to relax, catch the views, and soak in the ocean breeze, while Circuit Avenue is full of charming local restaurants and shops. The Oak Bluffs Town Beach and the Inkwell Beach are great for basking in the sun, swimming, and paddle-boarding further into the waters. The charming small town is also rich with history and culture, especially African American, while a true piece of history, the iconic Flying Carousel landmark is the oldest operating platform carousel in the United States, moved there from New York City in the 1880s. 


Aerial view of Provincetown in Cape Cod.

The "P-Town" is perched at the tip of Cape Cod with easy access from Boston by car or ferry. Packed full of live entertainment, local restaurants, and shopping, most shops are locally owned and operated. A know arts community, the town is home to more than 60 galleries and the Provincetown Art Association and Museum. The town's instantly recognizable feature and notable landmark, the Pilgrim Monument with its own local museum, is accessible via a glass-walled escalator tram from downtown. Winslow Street contains the former residence of Captain Ezra Cook, serving as a cozy and affordable bed-and-breakfast called the Howards End Guest House. The non-stop summer events include film festivals, CabaretFest, "PAWs" pet appreciation week, and the Provincetown Portuguese Festival. The next-door Cape Cod National Seashore has two excellent beaches, a bike trail, and fragile protected dunes.


The Witch House in Salem, Massachusetts.

The town is best known for its bloody history from 1692 to 1693 when more than 200 people were accused, and twenty innocent people were killed during the witch trials. Salem "embraces" its dark history by celebrating Halloween for all the 31 days of October. Set harborside on the north coast of Massachusetts also evokes a certain charm about the town's dark past, especially with the scenic harbor cruises, the cobbled pedestrian streets, the eighteenth-century ships in the harbor, and the attractive cemetery. For the fans of refined old buildings and quirky people, there's the Peabody Essex Museum, a witch trials memorial, and a Witch House where one of the magistrates lived and the preliminary examinations of the accused took place. The more neutral attractions include the Salem café, the oldest candy store in the US, and the Essex Street Pedestrian Mall. 


A feel of summer in Rockport harbor.
A feel of summer in Rockport harbor, Rockport.

An hour north of Boston, the endlessly photogenic Rockport would be a perfect still postcard from any angle if it wasn't for all the life brimming on the streets, despite being a dry (no alcohol) seaside village. Loaded with activities, it is a beloved summer getaway with tourists in mind but retaining New England's characteristic charm. There are galleries, gift shops, and BYOB restaurants in the harbor area, inclusive of the Motif No. 1. iconic red shack. Set on Bradley Wharf in the water, it was built when the town was becoming an arts settlement that is now open for visits and known around the world, especially within the art community. More active pursuits include kayaking in Cape Ann, and exploring the Rockport quarries, while the Halibut Point State Park offers waterside trails with splendid views all the way to New Hampshire and Maine

These towns are loaded with attractions, natural outings, endless sea vistas, and atmospheric downtowns. One will be submerged by a wholesome taste of Massachusetts upon visiting any one of them.

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