Oak Bluffs, Martha's Vineyard, taken by drone.

7 Tiny Off-Grid Towns In Massachusetts

The ancient New England state of Massachusetts has a rich history spanning Indigenous, Puritan, colonial, and Revolutionary War eras. The site of many of America's "firsts," the state is a travel destination on many people's lists, both from within the US and from abroad. Many people are familiar with the big-name tourist attraction cities like Boston, Salem, and Nantucket, but what some might miss, especially if they blink too hard, are the small, off-the-grid towns. These villages are hidden in the shadows of iconic mountains, nestled in the valleys of lush hills, or situated on the quiet eastern coast. They each have their own draws, and many have niche attractions that are unique to them, making them essential on your East Coast road trip.

Williamstown

The Thompson Memorial Chapel in Williams College, Williamstown, Massachusetts. Editorial credit: pics721 / Shutterstock.com
The Thompson Memorial Chapel in Williams College, Williamstown, Massachusetts. Editorial credit: pics721 / Shutterstock.com

The Berkshires are a stunning mountainous region in Massachusetts, extending into neighboring Connecticut, with lovely rolling hills, vibrant foliage, especially in the fall, and tiny rural villages like Williamstown, tucked off the grid and into the valleys. This charming town of around 5,000 residents is known as the "Village Beautiful," due to its delightful four-season surroundings and historic downtown area. Williamstown has a vibrant arts scene, home to several renowned art establishments.

One of these is the Clark Art Institute, a research center that doubles as a museum, most well-known for its displays of French Impressionist paintings, as well as works by famous American artists. Another well-known art center, the Williams College Museum of Art, is located on the campus of Williams College. They have an eclectic collection including American contemporary and Indigenous art, as well as photography and digital prints. Visual art is not the only focus here either, with the annual Williamstown Theatre Festival, a popular attraction for fans of stage performance. Williamstown is also home to Images Cinema, a local favorite for its showings of indie and foreign films, all in a historic building.

Stockbridge

Pedestrian street in Stockbridge, Massachusetts. Image credit danf0505 via Shutterstock
Pedestrian street in Stockbridge, Massachusetts. Image credit danf0505 via Shutterstock

Stockbridge, an ultra-charming archetypal New England village in the western Berkshires, is home to only 2,000 people. This town has everything one might envision when they daydream about a quaint Massachusetts village, including preserved 18th-century cottages and a classic, charming Main Street, complete with a landmark boutique hotel called the Red Lion Inn. This historic inn was built in 1773 and is widely considered to be haunted. Besides the superstitious appeal, it is a lovely stay with suites furnished with antique furniture, a restaurant, and a magnificent wraparound porch for guests to enjoy.

Stockbridge is also famously associated with the iconic artist Norman Rockwell, and the village is home to the Norman Rockwell Museum, which displays many of his original works, as well as educational exhibits about his life, particularly his time in Stockbridge, where he maintained a studio. Main Street also has some great galleries to purchase some works for yourself, including the Stockbridge Artisans Gallery. If you appreciate all the beautiful things listed so far, you certainly cannot miss the Berkshire Botanical Garden, an enormous, curated collection of diverse local plants and flowers, spread over 24 acres of stunning scenic grounds.

Ipswich

Ipswich Bridge over Ipswich River aerial view on Central Street in spring at town center of Ipswich, Massachusetts.
Ipswich Bridge over Ipswich River aerial view on Central Street in spring at town center of Ipswich, Massachusetts.

The hidden gem coastal town of Ipswich is engulfed in Atlantic Coast charm. It sits along the Ipswich River and is known for its long history, being an early Puritan town that was established way back in the 1630s. It still retains much of that colonial architecture, mixed in with gorgeous scenic surroundings like nearby Willowdale State Forest and Crane Beach, a conservation area with a pristine sandy beach. Despite Ipswich being a fun place for tourists to visit, and a quiet beach town alternative to some of the larger coastal cities nearby, the outdoor areas and calm town make it feel very off-grid.

Like many seaside villages, Ipswich is an ideal place to enjoy some fresh seafood. This town is specifically known for its clams and is famous for clam chowder, as well as local spots to try clams in various forms, such as the Clam Box, a local favorite. This counter-serve icon has been there since the 1930s, making everything from chowder to fried clams to a clam-filled take on the New England lobster roll. If you need a craft beer to accompany your salty snack craving, Ipswich Ale Brewery is the place, a highly recommended spot since the 1990s.

Great Barrington

A portion of Railroad Street in Great Barrington. Albert Pego / Shutterstock.com
A portion of Railroad Street in Great Barrington. Albert Pego / Shutterstock.com

On the border of New York in southwestern Massachusetts is Great Barrington, a small town with around 7,000 residents. Being on the edge of the Berkshires, it certainly retains some of the region's mountainside energy, both relaxing and full of life. It is a welcoming community, with a downtown dotted with fine dining restaurants like highly-rated Cafe Adam, serving contemporary American dishes in a chic but rustic atmosphere, and boutique shops like consignment shop Boho Exchange.

Due to its impeccable off-the-grid location, Great Barrington is also an ideal place for outdoor recreation. Nearby mountains offer skiing and hiking, including Monument Mountain, located on a reservation that spans over 500 acres. On and around the mountain are a ton of scenic trails, many of which lead to summits above the gorgeous Housatonic River Valley. Nestled in the valley is a peaceful River Walk, a well-maintained trail that goes through downtown and half a mile along the river.

Carlisle

Carlisle historic town center aerial view including First Religious Society church at 27 School Street and Town Common in historic town center of Carlisle, Massachusetts MA, USA.
Carlisle historic town center aerial view including First Religious Society church at 27 School Street and Town Common in historic town center of Carlisle, Massachusetts MA, USA.

Only 20 miles outside of Boston, the rural town of Carlisle, with a population of only 5,000, is an excellent escape from big-city life. The town is surrounded by huge conservation areas, making it feel extremely secluded despite being less than an hour from a large metropolitan area. One of these is Great Brook Farm State Park, a recreation area featuring over 20 miles of hiking trails, some of which lead to historic Native American cultural sites. It also features a working dairy farm on site, complete with an ice cream stand, making it a great place for fun and education to bring your family. Another public-use conservation area, the Great Meadows National Wildlife Refuge, also features numerous trails and an impressive wildlife observation tower about 25 minutes outside of town. For accessible outdoor recreation, the Malcolm Preserve is a great option, featuring paved trails that are wheelchair-accessible.

Deerfield

Beautiful village street in Deerfield, Massachusetts, USA. photo by emilyz21 via Shutterstock
Beautiful village street in Deerfield, Massachusetts, USA. photo by emilyz21 via Shutterstock

Deerfield is an immaculately preserved historic village in western Massachusetts, in the Connecticut River Valley. It is a unique place to visit because of its 18th-century atmosphere, which makes guests feel like they have walked into a time capsule from the 1700s. Across town, you will find 11 different living museums in various houses, providing a realistic glimpse into early American culture. Another historic marker is the mass grave site of the 1704 Raid on Deerfield, a pivotal event in colonial history when French and Indigenous armies attacked local colonists.

Less old and less morbid, perhaps, Deerfield also has several attractions that add to its hidden gem status. Mount Sugarloaf State Reservation is a lovely area off the grid for hiking, camping, picnicking, and enjoying some scenic, quiet time. Downtown, go shopping at the original Yankee Candle store, which absolutely retains its old New England charm. There are also two renowned breweries on the main drag, Tree House Brewing Company and Berkshire Brewing Company, making Deerfield a subtle destination for beer lovers.

Oak Bluffs

Sunrise over Oak Bluffs skyline, showcasing landmark houses and a dramatic winter cloudscape above Ocean Park on Martha's Vineyard, Massachusetts, United States.
Sunrise over Oak Bluffs skyline, showcasing landmark houses and a dramatic winter cloudscape above Ocean Park on Martha's Vineyard, Massachusetts, United States.

Located in the popular tourist area of Martha's Vineyard Island is the little town of Oak Bluffs, a sort of well-kept secret in favor of some of the more visited towns on Cape Cod. The town, home to around 5,000 residents, is a unique coastal destination, boasting a quiet harbor and charming old Victorian "gingerbread style" cottages that create a special experience for those who visit. The town is also deeply connected to African American cultural history, having served as a long-time cultural sanctuary for Black people, dating back to the era of segregation, with many notable icons, such as Langston Hughes and Adam Clayton Powell Jr., having resided there.

One of the places they probably enjoyed in Oak Bluffs was Inkwell Beach, which is a stop on the African American Heritage Trail, and is a beautiful place to swim, sunbathe, read, and reflect while listening to the calm waves from the sand or floating around in the gentle water. Within walking distance is the Flying Horses Carousel, the oldest platform carousel in the US, and a must-see for families with children, but great for all ages. Speaking of kids, they will be sure to love the desserts in this town, from decadent house-made chocolates at Ben & Bill's to freshly baked pastries at Back Door Donuts.

In these little off-grid towns...

You will find unique, truly niche experiences that cannot be found elsewhere in the state of Massachusetts, or anywhere, for that matter. Some of these, like the living history museums in Deerfield, or the immersion into the arts in Williamstown or Stockbridge, cannot be found in bigger cities. The slow-paced, peaceful enjoyment you can find in places like the less-crowded beaches of Ipswich and Oak Bluffs, or the conservation areas and state parks of Carlisle and Great Barrington, just does not exist in giant metropolitan areas. For these reasons and more, the little off-grid villages of Massachusetts belong on your travel bucket list.

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