11 Best Small Towns to Visit in Massachusetts
Talk of pretty beaches; some of the best in New England— or even in the whole country. All four seasons, complete with warm Julys and ice-cold Februaries. Sparkling lakes; some of which, like Lake Mattawa in Orange, are among the most beautiful in the United States. As to the historical significance of the Bay State, however, you will need to slightly change gears and wax a little bit more lyrical. You have probably read about the Battles of Lexington and Concord, for instance, and the famous 'shot heard 'round the world', — or you have not. Well, this is the battle that marked the start of the American War of Independence. It is one reason the United States is today an independent country and the leader of the free world. Now this is the exciting part - the state's amazing cornucopia of small towns, many of which feature the things we have highlighted. If this has piqued your interest, the following are the best small towns to visit in Massachusetts.
Concord
The year is 1775, and Massachussettes is restive — perhaps more restive than other colonies. Seven hundred regular British Army soldiers march to Concord. Their main objective is to disarm the anti-British rebel and destroy their arms and ammunition. But the Colonists get wind of it and are not about to accept a scintilla of humiliation. While historians have since argued about who fired the first shot at the Battle of Concord and Lexington, they have not argued about the impact of the first shot since described as the 'shot heard 'round the world." If you have the slightest interest in American history, a visit to Concord is something like a rite of passage. Yet Concord is not just a historical goldmine, complete with old wooden storefronts. It is also incredibly beautiful. If you want to relive the battle that triggered the Revolutionary War, reserve a full day at the Minute Man National Historical Park, located within the town.
Provincetown
Even those who have not set foot in Provincetown have read about it. Provincetown is a whole chapter in American history. It is in Provincetown, for example, where the Pilgrims, who were aboard the historic Mayflower, landed before finally wending their way to Plymouth. It is in this sense that the history of the United States is the history of Provincetown and of Massachusetts at large. Today, nestled at the tip of Cape Cod, Provincetown is essentially a resort town — and one that summer vacationers do not often seem to get enough of. Though only about 3,200 people call it home, Provincetown, because of its sandy beaches, its arts and culture scene, its innumerable art galleries, including the Rice Polak Gallery, the town's go-to venue for contemporary art, is hands-down among the best small towns to visit in Massachusetts.
Rockport
Rockport is exactly 43 miles from Boston. It is a road trip that should not take more than an hour. Yet if you visit Rockport from Boston, you will feel you are in a new world altogether. Named for the abundant granite in the area, Rockport is a pretty, laid-back town that captures the heart-melting beauty around the northernmost tip of Cape Anna. If you want to single out a part of Rockport worth exploring, it will have to be the iconic Bearskin Neck, a strip of land that juts out from the center of the town to the town's famous harbor. Plenty of art galleries and casual but classy restaurants dot this often vibrant stretch — while the cool, seaside ambiance is something you will want to stay with you forever. Just make sure when you are in Rockport, you grab a bite at Brothers Brew Coffee Shop and spend an idyllic evening at the Halibut Point State Park, a granite quarry turned lake that boasts picturesque trails and amazing ocean views.
Stockbridge
There will be no need to look up the meaning of the word "picturesque" in an Oxford dictionary, especially if you visit Stockbridge, Massachusetts, a famous eye candy curled up in the Berkshires of western Massachusetts. The town's beautiful Main Street was thrust into the public imagination by Norman Rockwell's "Home for Christmas," a heart-ravishing artistic masterpiece that still epitomizes the essence of Christmas in small towns across the United States, is a pleasure to stroll through — and one you will not want to turn your back on. It happens that Norman Rockwell, a celebrated illustrator best known for his covers for the journal The Saturday Evening Post, lived in Stockbridge for the last 25 years of his life. Today, Norman Rockwell Museum houses an impressive collection of the artist's original works and some carefully-selected memorabilia — and remains one of the town's most sought-after attractions.
Northampton
Northampton may not boast the history of a Concord or a Provincetown, but that does not mean it cannot be among Masschussettes' finest small towns. This stunner is home to about 28,900 residents and often strikes the sweet spot between the vibrancy of a big town — and the laid-back charm of a small one. If your idea of a good town is a bohemian college town that plays host to a decent population of hippies, Northampton is your answer. This is because Northampton is home to the prestigious Smith College, one of the best-ranked liberal arts colleges in the United States —and one of the largest of its kind for women in the country. For the best Northampton experience, find your way to Smith College Museum of Art, Thornes Marketplace (if you are an avid shopper), or, better still, the heart-tickling Smith College Botanic Garden — if you want to know what a botanical garden should look like.
Wellfleet
The East Coast, many will agree, is among the best places in the country to enjoy the finest seafood. And if you are a seafood connoisseur, you know where a plate of oysters stands in the seafood pecking order. Now that we are speaking of oysters, one of Wellfleet's claims to fame is its quality of oysters — besides just the number. Experts have attributed this to several factors, including the high salinity of the Cape Cod Bay area. If you want to prove this for yourself, you will need to order a plate of oysters at MOBY DICK'S, even if this will involve a wait. But if you are a beach bum, Marconi Beach will be at your feet, a popular blue-space gem set in the backdrop of gorgeous scenery.
Williamstown
Williamstown is secreted in the northernmost corner of the Bay State, about 168 miles west of Boston. This underrated Massachusetts secret is home to about 4,500 residents and, therefore, comes with the distinctive small-town charm you would expect of a town of a similar size. Known as the "Village Beautiful" and nestled in the Berkshires, a part of Massachusetts famous for its spectacular scenery, Williamstown is encircled by cascades of mountains and lush forests, features that lend it a lovely, rustic look that most vacationers often crave. After soaking up the town's cheerful atmosphere, you will want to check out the Williams College Museum of Art, one of the finest college art museums in the United States. Then again, the Sterling and Francine Clark Art Institute, or just The Clerk, houses a mind-bending array of French Impressionist paintings you will want to sample.
Edgartown
One of Edgartown's claims to fame is that it plays host to the first colonial settlement on the spectacular island today called Martha's Vineyard. To a history buff, this is enough reason to make the trip, if for nothing more than to step back into time and relive those early, heady moments. There are many ways to take in Edgartown's spellbinding beauty, a small charmer with a compact downtown area spread out on a stretch of land that is only about 35 square miles. However, nothing beats the feeling and the excitement of walking down Edgartown's quaint streets, especially towards the peaceful waterfront area, and admiring the classy seaside cottages around. Most of these cottages feature Greek Revival architecture, complete with elegant porches and rose gardens.
Nantucket
If you are looking for a Massachusetts town best suited for rest and relaxation, and a toe-in-the-sand experience, you will hardly go wrong with Nantucket, a town and island situated about 30 miles off the coast of Cape Cod. Whether you will want to gasp at the beautiful lighthouses within the town's proximity, sink your feet in the powder-soft sand that fringe the island's beaches, or just enjoy quiet moments in your own little world, Nantucket, once called "the best island in the world by National Geographic," will check every box. For a meal that will linger in your mind for long, enjoyed amid the light-hearted fun of live music, Cisco Brewers, located at 5 Bartlett Farm Road, is a Nantucket crowd-puller worth experiencing.
Sandwich
No, this is not Grilled cheese, the ooey-gooey sandwich 79% of Americans, according to 2019 data by YouGov, swear by. Sandwich is a beautiful seaside town occupying the eastern end of the Cape Cod Canal just east of Bourne. One of Sandwich's claims to fame is that it is the earliest European settlement on Cape Cod, a gorgeous peninsula known — not only for its miles of spectacular shoreline — but also for its mouth-watering lobster rolls and rich history.
While many old settlements have now become deserted ghost towns where swallows and owls build nests in abandoned houses, Sandwich is home to about 2,800 residents and boasts several historical landmarks such as the Hoxie House, arguably the oldest extant house "in the area". Then again, if you have the slightest interest in the history of the region, the Sandwich Glass Museum is a little piece of history that celebrates the town's glass-making heritage and presents excellent glass-blowing demonstrations almost every hour.
Chatham
Though Chatham, a Massachussettes secret located right on the elbow of Cape Cod boasts a population of only about 1,500 and is evidently tiny, especially if its population is anything to go by, it is so big on charm and character as to leave a first-time visitor completely astounded. Featuring classic Cape Cod architecture and an intimate, slow-paced ambiance, Chatham can make for a top-notch hideout. It is perfect for those who want to wind down in an idyllic, fairy-tale setting and boasts several attractions that will make a first-time vacationer start scouting for a realtor.
Aside from the Chatham Lighthouse, a working lighthouse —one of a few — a drive past some stunning homes, Chatham's other crowd-pullers include the Atwood Museum, an information-rich museum that reenacts the history of the area through beautiful handmade ship models — as well as Shark Center, where you will learn and unlearn much about of the most misunderstood sea creatures.
The Takeaway
While the whole New England shoreline is dotted with small towns, many of which are some of the most historic in the United States, the Massachusetts stretch is home to what could be the most dated, beautiful, and secluded. From big names such as Concord and Provincetown — to less-known ones such as Chatham and Sandwich, a small-town enthusiast can never curse his luck in Massachusetts. Here is the truth: The best small towns in Massachusetts are in a sense, the best small towns in the country.
