The Getaway
Enjoy The Delights of Small Town Massachusetts

Massachusetts has an abundance of delightful small towns, from foliage-laden destinations in the Berkshires to the coastal villages three hours to the east. Natural beauty and human creativity work hand in hand in the Bay State, where countless luminaries have found inspiration. You can plug into the wellspring with a well-timed trip filled with lighthouses, Louisa May Alcott novels, skiing, and protein from the deep. This is bear country, so you may even catch a glimpse of a dumpster-diving cub on a lazy midsummer day.

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01 Stockbridge

Empty path along a street on a cloudy autumn day. Stockbridge, MA, USA. AlbertPego/ Getty Images

Stockbridge is an idyllic town in the Berkshires that punches way above its weight in the art sphere. The Norman Rockwell Museum is based here, which is a big deal for fine art students and Lana Del Rey fans alike. And the acclaimed Lincoln Memorial sculptor Daniel Chester French lived and entertained at Chesterwood, now a National Trust for Historic Preservation site. While you're in the area, check out Charles H. Baldwin & Sons for pure vanilla, baking ingredients, retro toys, and other cool odds and ends.

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02 Ipswich

Looking over the Castle Hill and surrounding rolling hills, from the Great House, toward the Ipswich Bay. Ipswich, MA, USA sphraner/ Getty Images

Want to breathe in the salty air and get active out in nature? Ipswich is an underrated town an hour north of Boston, where you can bike or ride horses until your butt aches. If you prefer your own two feet, you can walk your dog along popular Crane Beach or hike the dunes and pitch pine forest. You can jump into the invigorating water when you're done guiding your steed or pumping your legs. While you're in town, check out the local wolf sanctuary, Wolf Hollow, and eat at the famous Clam Box.

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03 Provincetown

Old Harbour Life Saving Museum, Race Point Beach, Cape Cod DenisTangneyJr/ Getty Images

Cape Cod's Provincetown has long been a vibey LGBTQ haven and general summer hub. Its numbers swell during the warmer months thanks to an array of dining and entertainment spots, attractive shops, beaches, galleries, old cottages, and a cute walkable downtown area. Cycling here is safe and fun, so bring your gear or hire a bike from one of the P-town rental places.

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04 Newburyport

Newburyport is a small coastal, scenic, and historic city in Essex County, Massachusetts, United States, 35 miles northeast of Boston. DenisTangneyJr/ Getty Images

Newburyport, on Massachusett's North Shore, lies just 38 miles from Boston and 10 miles from Ipswich. The town's been inking many million-dollar property deals since the COVID-19 pandemic began. This is partly due to its accessibility, amenities, waterfront, and vibrant downtown area with high-end restaurants and boutiques. The Clipper City Rail Trail, an artsy walk along old train tracks, is a new attraction, and the Firehouse Center for the Arts and Maudslay State Park are two other places you can spend your leisure time. Newburyport was linked to the Underground Railroad and housed the first U.S. Coast Guard station.

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05 Rockport

Rockport is a seaside town in Essex County, Massachusetts, United States. Rockport is located approximately 40 miles northeast of Boston at the tip of the Cape Ann peninsula. DenisTangneyJr/ Getty Images

Rockport is a gorgeous, quaint town on the Cape Ann peninsula, and it's full of smiley locals and welcoming eateries. Bearskin Neck is your first port of call for gallery hopping and a meal. En route, you may notice former fisherman shacks. Motif No.1 is one such structure, and it's supposedly one of the most painted buildings in the world. The village has an interesting relationship with alcohol—restaurants can serve booze, but liquor stores are illegal. For vistas that reach as far as Maine and New Hampshire, head for Halibut Point State Park, then trek down to Front Beach for a swim.

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06 Chilmark

Menemsha is a fishing village located in the town of Chilmark on the island of Martha's Vineyard in Dukes County, Massachusetts. DenisTangneyJr/ Getty Images

Martha's Vineyard needs no introduction—this island in the Atlantic Ocean is beloved, and Chilmark, one of its six towns, has the most expensive residential real estate in New England. Chilmark is rural, with many of the trappings of an English hamlet, including grazing livestock, stone walls, and an undulating green landscape. Make your way to Menemsha for some shopping, a gander at the fish market, and a postcard-perfect sunset.

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07 Manchester by the Sea

Manchester-by-the-Sea is a town on Cape Ann, in Essex County, Massachusetts, in the United States. DenisTangneyJr/ Getty Images

Manchester by the Sea was plucked from relative obscurity when Casey Affleck won the Best Actor Oscar in 2017. The eponymous film was shot in the town and surrounding areas, but it wasn't the first time picturesque Manchester by the Sea appeared on the screen. Get acquainted with this fishing community and relax on Singing Beach, where the sand whistles when you walk on it.

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08 Nantucket

Harbor Houses in quiet and calm Sunset in Nantucket Island Bojan Bokic/ Getty Images

Nantucket, like Martha's Vineyard, has cachet. It's only 50 square miles, but many a summer memory has been made on the island, and celebs love to buy grand second homes here. You can eat your body weight in lobster rolls and scallops, mosey on up to the Daffodil Festival in spring, and have ice cream with a breeze blowing in your hair.

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09 Lenox

Autumn in the small village of Lenox, Massachusetts DenisTangneyJr/ Getty Images

Many of the small towns in Massachusetts are obsessed with art and literature. That theme continues in Lenox, a town Nathaniel Hawthorn and Edith Wharton once called home. The Boston Symphony Orchestra uses Lenox as a summer base, for example. You can engage with various forms of creativity or hunker down at the Miraval Berkshires wellness resort.

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10 Deerfield

The Bridge of Flowers spans the Deerfield River with the rolling hills of Western Massachusetts pics721/ Getty Images

Deerfield's historic district has multiple 18th-century homes. Together they form an outdoor museum where the community gathers for various live demos and classes. Once class is dismissed, you can clear your head on the Pocomtuck Ridge Trail. Celebrate your moderate workout with a snack on the bench overlooking the countryside.

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11 Concord

Concord, MA, USA - October 21, 2019: The Old North Bridge, a historical site in the Battle of Concord, the first day of battle in the American War of Independence. Photo by Katkami/ Getty Images

A quick 35-minute drive out of Boston, and you may end up in Concord. The town is renowned for its history and role in the Revolutionary War and its connection to Henry David Thoreau. Concord's Walden Pond inspired Thoreau's world-famous memoir, Walden. You can do various activities at the pond, including boating.

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12 Chatham

Stock photograph of a row of shops in Chatham, Cape Cod, Massachusetts, USA. benedek/ Getty Images

Chatham is another enchanting Cape Cod town with summer concerts, a still-operating 19th-century lighthouse called Chatham Light, and lovely beaches where you can watch seals and play in soft white sand. The Impudent Oyster has been feeding patrons for over forty years, so stop by to sample the goods when you're hungry.

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13 Great Barrington

Railroad Street, Great Barrington, The Berkshires, Massachusetts Barry Winiker/ Getty Images

Great Barrington is a Berkshire County town known for its getaway-worthy ambiance. The grocers and bakeries are fancy, farm-to-table restaurants are ready to serve you delicious fare, and the restored Mahaiwe Performing Arts Center offers movies and live performances. Bard College Simon's Rock campus is based in Great Barrington, so there's a youthful energy in the air to accompany the vintage buildings.

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14 Wellfleet

Wellfleet is a town in Barnstable County, Massachusetts, United States, and is located halfway between the "tip" and "elbow" of Cape Cod. DenisTangneyJr/ Getty Images

Foodies can head to Wellfleet to find some of the finest shellfish and seafood in the region. Mac's Shack is a trusty choice. There's an annual Oyster festival if you want to go all in on the mollusks and lemon squeezing. Go fishing to make your own catch, and burn off the extra calories at Cape Cod National Seashore or the Wildlife Sanctuary, which comprises woodlands, salt marshes, and an aquarium.

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15 North Adams

North Adams is a city in Berkshire County, Massachusetts, United States. It is part of the Pittsfield, Massachusetts Metropolitan Statistical Area. DenisTangneyJr/ Getty Images

North Adams is best known for Mass MoCa, one of the most significant visual and performing arts spaces in the country. But there's more to this charming Berkshire County town than its renowned museum. In fall, the leaf-peeping in Mount Greylock is exceptional. Natural Bridge State Park has a rare natural white marble arch, and you can also walk the Appalachian Trail.

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