12 Top-Rated Small Towns In Massachusetts

Few states represent the true spirit of America better than Massachusetts. The western part of the state is an outdoor paradise that teems with amazing spots for skiing, hiking, and other enjoyable adventure options. While Boston (except for the traffic) deservedly gobbles the limelight, this part of Bay State is star-studded with a plethora of quaint small towns that are pretty cool and lovely. The landscape around the Berkshires is particularly heavenly. On the other side of the state, most of the region has that heart-ravishing countryside feeling and the distinctive quaint New England town feel. If you were to pick a few choices, the following are 12 top-rated small towns in Massachusetts you should already be packing for.

Chatham

Often described as sitting on the elbow of Cape Cod, Chatham is a tasty town of about 1,500 that has  served as a setting for several award-winning movies, including "The Finest Hours" and the Netflix series "The Perfect Couple." Named for a town in Kent, England where celebrated writer Charles Dickens once lived, Chatham is incredibly beautiful and is often a preferred retreat for several Boston elites seeking seclusion, delicious views, and elbow room. You may want to embark on a boat ride and see Chatham Lighthouse from the water, haul some lobster traps, and see the crabs and starfish that come up, or just enjoy floating about and enjoying the thrilling experience. At the Fish Pier, you can see the seals and watch boats get unloaded — or find yourself in Nauset Light to stand in awe of a real surf. Finally, the Atlantic White Shark Centre, expected to reopen in 2024, is worth checking out. Do not forget to burn your legs at the rail trail to Harwich Center and beyond.

Provincetown

Only about 3,200 residents call Provincetown, a friendly, high-end Massachusetts eye candy that boasts one of the largest LGBTQ communities in the United States, home. P-town, as Provincetown is often fondly referred to, is usually ranked among the best beach towns in America. This means beach bums will be spoiled for choice because of the world of offerings.

But that said, Race Point Beach could be the prettiest around the area and is an amazing place for whale-watching, magical sunsets (best admired while wrapped in a blanket), and endless miles of rolling sand dunes. To break a sweat, and get some respite from the constant hum of Commercial Street, where art pours from every window, the Province Lands Bike Trail is worth considering. And as P-towners might agree, it will be hard to miss America's tallest all-granite structure — The Pilgrim Monument.

Concord

Forget about its other enticing attractions and draws. There is no experience that comes remotely close to that of setting foot where the first shots of the American Revolution were fired. This, ahead of others, is what makes Concord top-rated. The best way to explore the Birthplace of American Liberty is by opting for Liberty Rides, a spellbinding trip that will see you traverse the popular Old North Bridge — where courageous farmers once fired what has since gone down in history as "the shot heard round the world." Concord Colonial Inn, a feature of the town since 1716, is known to have stored provisions for the Concord Minutemen and hosted celebrated American essayist Henry David Thoreau. The Concord Museum, whose collection includes artifacts from Ralph Waldo Emerson, Louisa May Alcott's Orchard House, and the Thoreau Farm, all give a shrine-like experience that will leave literary enthusiasts completely blown away.

Northampton

It is not just Jenny Lind, the Swedish celebrity singer whose soprano voice is known to have elicited adulation from several art legends, including Mendelssohn — who fell into the spell of Northampton — and declared it “the Paradise of America.” Situated in the “Happy Valley” region on the west side of New England’s longest river, this top-rated Massachusettes gem boasts a population of about 28,900. Because it hosts Smith College, a long-standing institution reputed to be the largest privately endowed college for women in the United States, many find Northampton consistently vivacious and full of life. Thanks to the college, Northampton plays host to attractions such as Lyman Plant House and Conservatory, which boasts one of the largest collections of tropical and desert plants on the East Coast. Another legacy project of Smith College is the 153-year-old Smith College Museum of Art, a deceivingly small facility that houses some of the finest art exhibits, including some works from Picasso.

Deerfield

Deerfield is a sumptuous slice of Massachusettes that is secreted in the northern Pioneer Valley along the Connecticut River. One of Franklin County’s oldest towns boasts a main drag that features lush, tree-lined streets where several Colonial-era homes still stand. A visit to this New England charmer will feel like stepping back into time. In 1704, this town was the scene of the Deerfield Massacre, the bloodiest event of Queen Anne’s War. Today, Deerfield still evokes the feeling of being on the frontier. Historic Deerfield is smack in the middle of the town and features up to 12 well-preserved antique houses some of which date back to the 1730s. These include the historic Deerfield Inn, a feature of the town since 1884. Visitors will enjoy traipsing through the Magic Wings Butterfly Conservatory & Gardens as well — where one can rest while admiring thousands of colorful butterflies.

Great Barrington

The fact Great Barrington is located in the Berkshires should alone make it a top-rated town. The Berkshires is in the western region of the Bay State and is world-renowned for its spellbinding natural beauty and delicious vistas. Monument Mountain, one of Great Barrington’s frames, offers spectacular views of the area. Celebrated literary greats such as Nathaniel Hawthorne and Herman Melville are known to have hiked the mountain in adventures that sparked the penning of Moby Dick, a masterpiece reputed to be a cornerstone of modern American literature. For more scenery and goosebumps, an evening stroll along the River Walk, with the Housatonic River in plain view, will be a must-do. For art aficionados, the Mahaiwe Performing Arts Center, a Great Barrington staple since 1905, hosts some of the world's greatest artists.

North Adams

Deceivingly small, and boasting a population of just about 12,700, North Adams is big on charm, attractions, and character. Also located in the Berkshires, a natural outdoor paradise that teems with 360-degree heart-melting views, one of North Adams’ claims to fame is the fact it plays host to the Massachusetts Museum of Contemporary Art, the largest contemporary art museum in the United States. Housed in an old mill building, that would still be a sought-after attraction even if it were empty, this museum boasts a diverse collection of thought-provoking exhibits and installations — that pushes the limits of creativity to unimaginable levels. 

Mount Greylock, the tallest summit in the state, is just about 10 miles away. Whether you want to hike or bike, this panoramic spot has you covered. Finally, the scenic trails and beautiful marble rocks at the idyllic Natural Bridge State Park — offer a rich visual repast that will remain etched in the memory for a long time.

Newburyport

Full of views that will soften any heart, Newburyport is a Massachusetts stunner of about 18,200 residents that occupies a picture-perfect spot where the Merrimack River meets the world’s second-largest ocean. Once a prosperous ship-building hub, this town still brims with nautical treasures, including the nearly 190-year-old Custom House Maritime Museum, which houses awe-inspiring ship models and replicas, including Nao Trinidad, a spectacular replica of Magellan's ship. Plum Island Lighthouse is stunning, especially if viewed at night or in the evening — while the 4,700-acre Parker River National Wildlife Refuge Gatehouse, with its picturesque trails, sand dunes, and beach access, is a magical spot that will tickle the fancy of an outdoor enthusiast. Sunsets at Parker Rive are particularly known to be heavenly.

Manchester-by-the-Sea

Tucked away a convenient 30 miles from The Hub, approximately, in an area once known as the “North Shore,” Manchester-by-the-Sea often makes for an idyllic city escape. While this cute, little town of fewer than 6,00 residents had largely remained unknown, and hence criminally neglected, the production of an award-winning movie by the same name, filmed in the same town, would catapult it into the public limelight. At Masconomo Park, which overlooks the town’s picturesque harbor, first-time visitors will enjoy watching the boats passing by and gasping at the beautiful views around. The Tucks Point Rotunda, designed by famed Boston architect E.A.P. Newcomb, offers beautiful harbor views and will be worth checking out. Finally, by its name alone, Singing Beach should be an object of curiosity. It is a fine place to walk barefoot while feeling the warmth and texture of the sand.

Rockport

Known for its active art colony, Rockport is a top-rated Massachusetts treasure that plays host to a population of about 4,800. It sits at the northernmost tip of Cape Ann — about 43 miles from Boston. Expect to traipse through one of the oldest art colonies in the United States. Built at the turn of the 19th century as a storage space for lobstermen — is a red shack reputed to be America's most-painted building  — Motif #1. You will want to keep your camera a bit busy here while enjoying the tranquility of the immediate environment. If craving lobsters, the Fish Shack Bar & Restaurant, with its beautiful waterfront views, serves classic New England seafood of a wide variety. For some tasty art, however, whether pottery or paintings, the iconic Bearskin Neck is the go-to stretch.

Stow

Whether sweet or tart, red or green, nothing compares to the experience of lustily sinking one’s teeth into the flesh of a perfectly ripe, succulent apple. It happens that Stow, a town of about 7,100 located just about 30 miles west of Boston, is best known for its numerous apple orchards. Expectedly, this makes fall the best time to visit this photogenic town. Pilot Grove Farm will especially be worth checking out, as it sits on what was once one of the town’s original twelve lots. If looking for something bigger but more intimate, Honey Pot Hill Orchards includes hay rides, wildlife viewing (including ponies and goats), and several field trips — in addition to apple-picking. At the American Heritage Museum, you can chance on a WW II battle reenactment, besides exploring the intriguing military artifacts, including current tanks and modern armored vehicles.

The Takeaway

For its history, culture, and heritage, few states are as American as Massachusetts, the sixth state to join the Union and one of the original thirteen. The Bay State is so start-studded with historic small towns, that it is nearly impossible to pick the most top-rated. Still, gems such as Provincetown, home to America's tallest all-granite structure,  Rockport, which hosts one of the oldest art colonies in the United States, and Concord, the Birthplace of American Liberty, will top any list.