The 16 Best Charming Small Towns in Massachusetts

• Why I Recommend It: wellness retreats at Kripalu Center, Norman Rockwell memorabilia, accessible from NYC by bus
• Where to Stay: Stockbridge Cabin (from $328/night, sleeps 6); Berkshires Forest Retreat (from $388/night, sleeps 7); GreenHouse (from $144/night, sleeps 4)

Perhaps you’ve heard of the Berkshires? The Western Massachusetts destination is a fixture on The Real Housewives of New York City. Though, I can’t imagine anyone affiliated with this rural region wishes to be associated with the unseemly antics that go down at Dorinda Medley’s estate. Instead, the better connection is to Norman Rockwell. The American painter spent the last 25 years of his life deriving inspiration from Stockbridge. This pretty-as-a-picture town oozes charm and history with the backdrop of rolling hills. Obviously, you’re going to stop by the Norman Rockwell Museum. Be sure to check out Naumkeag, a botanical garden and Gilded Age mansion, too.

“Stockbridge is great because it's easily reached via bus from NYC, and feels a world away—like a fairy tale hamlet in the woods,” says PureWow Senior Editor Dana Dickey. “I highly recommend signing up for a wellness retreat at the Kripalu Center where programs center on yoga and spiritual growth. Maybe it's the meditation, maybe it's the clean air and bright stars amid the quiet countryside, but you won't leave this town without feeling happier and more relaxed.”

• Why I Recommend It: thriving LGBTQ+ community, tons of activities including restaurants, nightclubs, beaches and galleries
• Where to Stay: Modern Beachfront Condo (from $250/night, sleeps 2); Sailor’s Den (from $112/night, sleeps 2); Provincetown Home (from $169/night, sleeps 4)

Perched at the northern tip of Cape Cod, Provincetown (P-town if you’re a local or frequent visitor) is a summer hotspot. The year-round population clocks in around 3,000, but that swells to 60,000 during peak season. Don’t let that deter you. This endearing seaside town has a rich history of progressiveness and inclusion that’s long lured artists, poets, entertainers and members of the LGBTQ+ community. Provincetown is famed for hosting epic Pride festivities, including its annual parade. While you’re there, def hit the galleries, nightclubs, restaurants, indie shops and beaches and grab a drink at A-House, the oldest gay bar in the United States.

“Provincetown is a gorgeous queer haven where LGBTQ+ families—and singles—can be seen roaming the shop-lined streets,” says PureWow Vice President of News & Entertainment Philip Mutz. “This isn't so much a beach town (the beaches are surprisingly hard to access) as it is a lively, bustling community. Come for the art and the shopping, stay for a drag show at the Crown & Anchor and a martini at Monkey Bar. Oh, and be sure to do your research in advance because many weeks are theme weeks (unless you like being surprised).”

• Why I Recommend It: rich (and spooky) history, great breweries, scenic harbor
• Where to Stay: The Creaky Cauldron (from $164/night, sleeps 8); The Violet Suite (from $149/night, sleeps 2); The Langmaid House (from $155/night, sleeps 2)

Salem, which is notorious for its 1692 witch trials in which more than 200 people were accused of practicing hocus pocus, casts a spell on all who visit. (Sorry, that was just wicked easy.) Not just a place to spend Halloween and learn about America’s most famous witch hunt, this coastal city that feels a lot like a town on the north coast of Massachusetts has a lot going for it that no one really talks about. So we will do a little bragging on behalf of the Essex Street Pedestrian Mall, scenic harbor cruises and the Peabody Essex Museum.

“Salem is full of cobbled hills and alleyways lined with gorgeous homes dating back a couple of centuries,” says PureWow assistant editor Delia Curtis. “You’ll find everything from quaint coffee shops like Gulu Gulu Cafe or the Ugly Mug Cafe to shops that cater to filling a witch’s arsenal with crystals and herbs like Haus Witch or The Coven’s Cottage. Get your tarot cards or astrological chart read, stomp through any of the many graveyards, saunter through The Witch House, or post up for a brew in one of their many local watering holes. My pro-tip as a Bostonian is to visit in the off-season if you’re not specifically looking to go around Halloween. Try for August or September to enjoy the fall activities without the massive crowds, or do and envelop yourself in the Jack-O-Lantern-filled joy of spooky season. You might even see a hearse at the local Dunkin Donuts like I did as a kid.”

• Why I Recommend It: close proximity to Boston, Hammond Castle, Good Harbor Beach
• Where to Stay: Annisquam Village Bunny Cottage (from $225/night, sleeps 3); The Gilbert (from $190/night, sleeps 2); Loft Townhouse (from $190/night, sleeps 5)

“When I was in college, I drove to Gloucester for an afternoon on a freezing fall day,” PureWow Associate Editor Marissa Wu recalls. “It was beautiful—glassy water, clear blue skies, the smell of salt in the air. We walked through the harbor, which is a maritime museum now, and saw the Fisherman’s Memorial.”

The quaint seaside town is a 45-minute drive north of Boston and is pronounced “glaw-ster” in case you were wondering. Though small, it’s rife with historical landmarks and attractions, such as the Cape Ann Museum featuring the work of the 1800s maritime artist Fitz Henry Lane. There’s also the 1920s medieval Hammond Castle and the Eastern Point Lighthouse. You’ll want to catch a sunrise on the water and walk the docks, which themselves are laden with fishing gear.

• Why I Recommend It: luxe health and wellness getaway, vibrant fine dining scene, top-rated arts and culture
• Where to Stay: Heart of Lenox Cottage (from $399/night, sleeps 4); Stonover Estate Guest House (from $205/night, sleeps 2); Main Street Apartment (from $225/night, sleeps 4)

Another small town that’s nestled in the Berkshires of Western Massachusetts, Lenox is a low-key cultural dynamo that’s surrounded by winsome scenery. Besides outdoorsy enticements such as Pleasant Valley Sanctuary, it’s brimming with fine dining restaurants (Cafe Boulud  has notably received rave reviews from patrons) and interesting attractions like The Mount, Edith Wharton’s Home (pictured above). Lenox is also home to Shakespeare & Company (so it goes without saying that you’re going to see a play) as well as Tanglewood, the summer headquarters of the Boston Symphony Orchestra.

“Lenox gets my vote as a worthy visit for luxury health and wellness retreats at Canyon Ranch Lenox, where you're led through health and weight loss programs with exercise, massages and the latest tech,” Dickey says. “It’s pricey, but the combination of top-level intel and attention amid clean air and crunching leaves is an investment in yourself. I have never slept so well as after I had reiki at Canyon Ranch Lenox.”

• Why I Recommend It: tons of art galleries, beautiful scenery, lobster rolls
• Where to Stay: Cape Ann Home (from $478/night, sleeps 10); Rockport Loft with Ocean Views (from $260/night, sleeps 3); Rockport Condo (from $151/night, sleeps 3)

Like a postcard come to life, Rockport is endlessly photogenic—and dry (yes, that means no alcohol)—seaside village with loads of characteristic New England charm and a population of 7,500 residents. This beloved summer getaway (which, we should mention, also wows in the fall, winter and spring) offers a blend of cute touristy and local stuff. Number one on the agenda: Eat your weight in lobster rolls. Not a tough gig, considering that you’re not in want of a seafood shack. Try Roy Moore’s, The Lobster Pool and Feather and Wedge. Then, hit up one of the dozens of art galleries, which rep hundreds of local artists. A couple good ones to start with are The Art Nook, David Arsenault (a realist oil painter) and the area of Bearskin Neck. Besides the galleries, gift shops and BYOB restaurants in the harbor area, go see Motif No. 1 (pictured above) and strike out on the waterside trails in Halibut Point State Park for splendid views that extend well into New Hampshire and Maine.

• Why I Recommend It: slice of literary and Revolutionary War history
• Where to Stay: Cottage Suite (from $100/night, sleeps 2); Hedy’s Lovely Home (from $90/night, sleeps 4); Carlisle Loft (from $105/night, sleeps 4)

Concord is undeniably one of the prettiest small towns in New England and perhaps best known as the site of the first battle of the Revolutionary War. First up on your history crawl? Minuteman National Historic Park to hike, glimpse the North Bridge (pictured above) and enjoy a picnic lunch. But this town isn’t solely for the American history buffs. Lit nerds, eat your hearts out. You can visit The Old Manse, where poet Ralph Waldo Emerson drafted his essay “Nature” in 1800, as well as Walden Pond, made famous by writer Henry David Thoreau and widely considered to be the birthplace of the American conservation movement. Cap things off with a trip to Louisa May Alcott’s Orchard House. (You may know her as the author of Little Women.)

• Why I Recommend It: iconic summer destination, unique architecture, great beaches
• Where to Stay: Luxury Yurt (from $200/night, sleeps 6); The Nest (from $275/night, sleeps 4); The Blue Lagoon (from $515/night, sleeps 6)

The idyllic town of Oak Bluffs earns our vote as *the* place to stay on Martha’s Vineyard. With Ocean Park, Circuit Avenue and Joseph Sylvia State Beach—a two-mile stretch of soft sand and shallow water that served as a filming location for the 1975 flick Jaws—to explore, plus the oldest operating platform carousel in the country, you may never even make it to Edgartown. (Oh well, there’s always next time.) Oak Bluffs is rife for exploring, and I’d start at the Gingerbread Cottages, a slew of vivacious Victorian homes that look like something straight out of Hansel and Gretel. The Flying Horses Carousel is another visitor favorite, as is The Sand Bar, open seasonally. Guess that’s why everyone from the Obamas and the Clintons to celebrities like Spike Lee have escaped to this quintessential New England summer retreat.

• Why I Recommend It: one of Cape Cod’s most beautiful towns, lots of outdoor activities
• Where to Stay: Chatham Windmill (from $250/night, sleeps 2); Downtown Chatham Home (from $299/night, sleeps 5); Cozy Cottage (from $225/night, sleeps 2)

If you’re a fan of sun-drenched beaches, Chatham is one of the most charming small towns in Massachusetts. It boasts some of the most gorgeous coastal spots in all of Cape Cod (and that’s saying something), plus a quaint downtown. After catching some rays or going for a leisurely stroll, spend the afternoon browsing the cute shops and savoring seafood at top-notch restaurants like Impudent Oyster (we hear the bacon-wrapped scallops are delish). You’ll definitely want to carve out some time to visit the Monomoy National Wildlife Refuge, the Atwood Museum, the Shark Center and the Chatham Lighthouse.

• Why I Recommend It: quintessential summer destination, charing architecture
• Where to Stay: Historic District Home (from $379/night, sleeps 5); Madaket Beach House (from $1,750/night, sleeps 10); Charter House (from $800/night, sleeps 8)

Despite being a relatively small state, Massachusetts counts two of the most iconic East Coast summer beach getaways among its lengthy roster of must-visit destinations. I’ve already discussed Martha’s Vineyard. Now it’s time to dive into the adorableness that is Nantucket. (For the sake of clarity, it’s worth mentioning that both the town and island share a name.) In my opinion, this is the most charming small town in Massachusetts, with its classic cottages dripping in hydrangeas come summertime. This legendary escape off the coast of Cape Cod attracts well-heeled holiday goers with its wind-swept dunes, cedar-shingled houses that belong on the cover of Architectural Digest and perfectly preppy atmosphere. Cobblestoned streets, upmarket boutiques, seafood eateries and historic churches are also part of the package. My ideal itinerary: Nantucket Whaling Museum, Brant Point Lighthouse, Sconset Bluff Walk and ice cream at The Juice Bar.

• Why I Recommend It: historical significance, naturescapes, antique shops
• Where to Stay: The Garden (from $244/night, sleeps 5); Quaint Newburyport House (from $315/night, sleeps 4); City Loft (from $239/night, sleeps 7)

When I think of adorable small towns in Massachusetts, Newburyport instantly springs to mind. Located 50 minutes from Boston, this coastal gem has a long history dating back to the Revolutionary War. Afterward, abolitionism gained popularity and it became an important stopping point on the Underground Railroad. All its appeal certainly isn’t in the past. Today, Newburyport flaunts a mix of modern and old-fashioned delights. Whale watching tours speak to its maritime roots, as does the Custom House Maritime Museum. You’ll also find a bevy of antique shops, including Oldies Marketplace, The Cottage and Green Plum Vintage Goods. Pick up a scoop of ice cream from Harbor Creamery before walking the scenic trails in Parker River National Wildlife Refuge and meandering down the boardwalk.

• Why I Recommend It: vibrant cultural scene, outdoor activities
• Where to Stay: North Street Nest (from $132/night, sleeps 5); Tree Top Suite (from $118/night, sleeps 2); NoHo Condo (from $215/night, sleeps 4)

A funky, crunchy, bohemian haven with tons of culture and strong left leanings, Northampton is a stomping ground for artists, authors, musicians, activists, students and academics. Much of the activity centers around Smith College, which has an art museum and a beautiful botanical garden. There’s also plenty of attractive architecture to admire, bookstores worth browsing, Thornes Marketplace, concerts at Academy of Music Theatre, the R. Michelson Galleries and everything from pedal boating to mini-golf in Frank Newhall Look Memorial Park. Meanwhile, cycling enthusiasts can bike the Norwottuck Rail Trail.

• Why I Recommend It: underrated coastal destination, Crane Estate
• Where to Stay: Historic Downtown Apartment (from $145/night, sleeps 7); Fourshe Villa (from $402/night, sleeps 9); Garden Getaway (from $150/night, sleeps 4)

Ipswich might just be the most underrated destination on our list. You’d think a place that’s packed with New England traditions and charm would be a bonafide tourism darling. To be clear, it’s not like Ipswich is some best-kept secret. But coastal towns like Rockport and Newburyport certainly get top billing. What the masses don’t know is their loss and your gain. Because it means more space to sprawl out on Crane Beach, fewer tourists at Castle Hill on the Crane Estate, shorter waits at restaurants and the chance to explore Sandy Point State Reservation sans crowds.

• Why I Recommend It: easy access to Martha’s Vineyard, extensive walking paths, kid friendly
• Where to Stay: The Deepwood (from $158/night, sleeps 6); Woods Hole Modern Marvel (from $357/night, sleeps 8); Great Bay Cottage (from $123/night, sleeps 2)

Heading to the Vineyard? Bundle it (or make it a weekend) with Falmouth, home to the Island Queen Ferry that delivers you to the Island in 35 minutes. Don’t write off this town for its snazzy neighbor, though. Falmouth has much to offer, from trails and walking paths (Shining Sea Bikeway and The Knob), to golf at The Cape Club, kid-friendly activities at Woods Hole Science Aquarium and St. Barnabas Memorial Church, which will take you straight to the English countryside. Wine aficionados will want to schedule a tasting at Cape Cod Winery, founded and run by an Italian family growing European grapes, while local foodies will enjoy a stop at Coonamessett Farm to peruse the stands, harvest some produce and enjoy a lunch outdoors.

• Why I Recommend It: Cape Cod’s oldest town, great museums
• Where to Stay: Water’s Edge Hideout (from $244/night, sleeps 7); Cape Carriage House (from $230/night, sleeps 7); Waterfront Historic Cottage (from $566/night, sleeps 9)

Sandwich boasts the distinction of Cape Cod’s oldest town, with a sizable population of just over 20,000. As is typical of the region, the beaches, particularly Town Neck Beach, are filled with soft sand, and the waters are tranquil. If you prefer a stroll, the Sandwich Boardwalk stretches across the marshy landscape, offering sweeping views. The Heritage Museum & Gardens combine architecture (including a centuries-old windmill and a hand-carved carousel) with nature (think seasonal gardens and a maze). Stop at Sandwich’s oldest house, Hoxie House (open seasonally) and then pick up some local provisions from Green Briar Nature Center & Jam Kitchen before watching the glass-blowing at The Sandwich Glass Museum. And when you’re ready for a sit-down meal, you can’t beat The Fishermen’s View. (Get a lobster roll, stat.)

• Why I Recommend It:
• Where to Stay: Modern Lakefront House (from $225/night, sleeps 4); High Grass Farm (from $181/night, sleeps 6); Waterfront House (from $225/night, sleeps 8)

Sturbridge is a quintessential New England village, and is embodied in the town’s Old Sturbridge Village. Set on over 200 acres are 40 historical buildings and costumed historians roaming the grounds, giving you a taste of rural life in the 19th century. Depending on the day, you might find the blacksmith or cabinet maker; perhaps you’ll run into the printer or potter or stumble into the garden—complete with cattle. When you’re ready to return to the 21st century, head to the Worcester Art Museum for art spanning Roman mosaics to Japanese prints. Sturbridge is also rife with antique and speciality shops, so if you love a good thrift and/or quirky goods, put Vintage and Swoon, Sturbridge Antique Shops, Sturbridge Pottery and Ox & Yoke Mercantile on your list. (And hot tip: Hyland Orchard is the place for apple picking come autumn.)