The 42 Most Charming Small Towns in Massachusetts
"Hearst Magazines and Yahoo may earn commission or revenue on some items through these links."
Massachusetts might be one of the country's smallest states, but it more than makes up for it with its postcard-worthy small towns, cities, villages...you get the pretty picture.
So while Boston is great for a dose of big city life, there's no shortage of coastal enclaves to explore, whether on a luxe, once-in-a-lifetime trip to Nantucket or a weekend spent in quiet fishing villages known for the freshest seafood. (Lobster rolls, anyone?)
Don't want the beach? No problem! Lace up your hiking boots to conquer mountains and scenic trails in the Berkshires. Massachusetts is also a dream for history buffs—after all, it was the birthplace of the American Revolution and the setting of the Salem witch trials.
Without further ado, here are our favorite charming small towns in Massachusetts, from artsy enclaves to preppy seaside villages.
Chatham
For a seaside escape with pristine beaches and an elite shopping experience, Chatham is your spot. Surrounded by water on three sides, this Cape Cod town is chock-full of inlets, sandbars, and coves. Those who prefer life on land will swoon over the prime real estate and the mile-long Main Street full of boutiques and eateries.
Newburyport
Sure, Newburyport is technically a small city, but it's packed with enough charm to rival even the tiniest towns in Massachusetts. Kick off your visit with a picturesque stroll through Market Square, where independent shops reign supreme—and if you're still in a shopping mood after that, nearby Tannery Square has been named one of the best shopping destinations in the state. End your trip with a once-in-a-lifetime meal at the top of the Newburyport Lighthouse, which can be rented out for parties of up to four.
Rockport
A lobster lover's paradise, Rockport is awash with seafood shacks offering everything from lobster rolls to fresh oysters, scallops, and shrimp. For a no-frills meal that doesn't skimp on the lobster meat, try Roy Moore's or Lobster Pool—and get your meal to go so you can whale watch at the harbor while you eat.
Stockbridge
If you ask us, this quaint main street is reason enough alone to visit Stockbridge. But no trip is complete without exploring Gilded Age estates like Naumkeag and Chesterwood, both famous for their vast gardens and historic architecture. Don't leave without touring the Normal Rockwell Museum, which features the world's largest and most significant collection of the artist's work.
Nantucket
For an idyllic summer experience right out of an Elin Hilderbrand novel, hop on a ferry to Nantucket for a weekend of wandering cobblestone streets, gazing at cedar-shingled cottages, and picnicking on windswept beaches. There's something on Nantucket for everyone: Restaurants like Cru and Galley Beach deliver an upscale dining experience for foodies, while history lovers will enjoy the Nantucket Shipwreck and Lifesaving Museum.
Falmouth
No trip to Cape Cod is complete without a visit to Falmouth, located on the upper Cape. Rent a bike and cruise around the Shining Sea Bikeway, a 10-mile path with top-tier views of Falmouth's beaches, harbors, and cranberry bogs.
Oak Bluffs
Oak Bluffs, a historically Black community on Martha's Vineyard, pairs beachside bliss with candy-colored cottages that look like they came straight out of a storybook. (Stroll around Ocean Park for the best views of both!) Movie buffs can sneak a peek at film history with a visit to Joseph Sylvia State Beach, which appeared in Jaws.
Woods Hole
Located within the town of Falmouth, this idyllic enclave deserves a shoutout all its own. The Nantucket look-alike is home to the ferry terminal to Martha's Vineyard, so it's the perfect pit stop for a picturesque bike ride, boutique shopping, or a meal at harborside Landfall, pictured here.
Hyannis
Hyannis is technically the largest village in Cape Cod, but it has an undeniable small-town feel. Presidential history buffs will want to visit the John F. Kennedy Hyannis Museum for a look at the first family's summer vacations. And Hyannis has a ferry to Nantucket, which makes it an ideal locale for island hopping.
Orleans
Nestled between the churning Atlantic and the tranquil Cape Cod Bay sits Orleans, a charming beach town full of cedar-shingled buildings and a beach for every mood. If you're looking for adventure (and are experienced!), try Nauset Beach, famous for its large waves. Skaket Beach, on the other hand, tends to offer calmer waters for a more tranquil vibe. After you dry off, stroll down Main Street for shopping and seafood.
Salem
There's something in Salem for everyone, whether you're a scaredy-cat (no shame!) or can't get enough of spooky season. Known for its witchy history, no visit is complete without stopping by the Witch House at Salem, Custom House, and the House of the Seven Gables. But Salem is a fishing town too, so grab a drink at one of many craft breweries before enjoying the catch of the day.
Sandwich
It's no wonder that a place named Sandwich has great restaurants: Try The Dan'l Webster Inn Restaurant or Fishermen's View for some of the best seafood Cape Cod's oldest town has to offer. And don't forget to grab dessert at Ice Cream Sandwich. After exploring historic sites like the Hoxie House and the Sandwich Glass Museum, cozy up in one of the town's historic inns or bed-and-breakfasts.
Edgartown
Talk about postcard-worthy! There's no better background for a photo op than the boutique-filled streets or the lighthouse in this Martha's Vineyard village. For the best views, rent a Jeep to off-road along the beachside trail that connects Edgartown and Oak Bluffs.
Plymouth
The coastal town of Plymouth is teeming with history and charm, featuring Leyden Street—first inhabited by the Pilgrims in 1620—Plymouth Rock, and a recreation of the Mayflower II. Beyond history, there are waterfront restaurants aplenty, whale-watching cruises, and 100 shops.
Manchester-by-the-Sea
You've probably heard of the Oscar-winning film Manchester by the Sea, so why not plan a visit to the town that inspired the flick? Although this fishing town is tiny (with less than 5,000 residents), it's home to miles of picturesque shoreline. Before heading to Singing Beach, visit Manchester By the Book for a beach read.
Provincetown
Provincetown is the oldest continuous art colony in America, so you'll never run out of galleries and exhibits to visit while wandering down the East End. The town is also known to be a wonderfully welcoming destination for the LGBTQ+ community, with festivals and parades held nearly every week in the summer.
Lenox
Who knew Massachusetts was home to such vast literary history? Tour The Mount, Edith Wharton's summer home, where she penned classics like House of Mirth and Ethan Frome. (Winter visitors can even take in the estate's legendary Christmas light displays.) To keep the Gilded Age theme going, there's Ventfort Hall, a recently restored mansion and a museum full of historical details.
Ipswich
For a local destination that feels like Europe, try Ispwich, home to Castle Hill. The property served as farmland for years before it was purchased by a Chicago businessman who built an impressive estate across 3,500 acres. A Castle Hill tour includes a peek into the Great House, various gardens, and access to the shoreline and hiking trails surrounding the property. Visitors can even book a stay at the inn on the grounds, pictured here.
Williamstown
College towns are typically rife with culture, and Williamstown, home to Williams College, is no exception. The campus is full of Gothic buildings that will make any architecture junkie drool, and art lovers will love spending hours in the Clark Art Institute. Thanks to a prime location on the Appalachian Trail, it's also a hiker's paradise.
Marblehead
For a coastal getaway less than 20 miles outside of Boston, try Marblehead. It's been said that walking down the cobblestone streets feels like going back in time, since more than 300 of the town's buildings have been preserved from the colonial era. Book your trip around the holidays to take in the Marblehead Christmas Walk lights.
Westport
Expect scenic views and idyllic rural dining on your trip to Westport, where there's both rolling farmland and waterfront real estate. Pop into the Westport Rivers Vineyard and Winery to try local wine. If you're more of a beer drinker, plan a visit to dog-friendly Buzzards Bay Brewing.
Vineyard Haven
Vineyard Haven is a hidden gem on Martha's Vineyard with a small-town feel. No trip to this town is complete without swinging by the original Black Dog, one of the most recognizable symbols of Martha's Vineyard. There are locations along the East Coast, but there's something special about visiting the original tavern, which now features a general store, café, and bakery. Don't forget to set aside time to relax on the beach with a new read from Bunch of Grapes.
Truro
Truro's designation as the Cape's "sleepiest" community means it's a go-to place for rest and relaxation. Its claim to fame: Highland Light, pictured here, known as Cape Cod's first lighthouse. Book a stay in one of Truro's beachfront cottages and venture out onto the scenic backroads. (Truro has the most in Cape Cod!) This quiet town packed with natural beauty is also a haven for artists, who can sign up for a painting, sculpture, or ceramics workshop at the Truro Center for the Arts.
Great Barrington
Ski bunnies, take note: Add Great Barrington in the Berkshires to your bucket list. And for cozy après-ski dining and shopping, bundle up for a jaunt down Railroad Street, one of the oldest streets in the country.
Northampton
Northampton lives up to its "Paradise City" nickname with its bustling music, dining, and arts scenes. For the best blend of city and country, spend your morning kayaking on the Connecticut River before seeing a Picasso at the Smith College Museum of Art—for free!
Gloucester
Under an hour from Boston, the home of America's oldest seaport offers adventures by land and by sea. Gloucester is the home base for National Geographic's Wicked Tuna's bluefin tuna captains, and avid viewers can hop aboard one of the boats to learn the ins and outs of the industry. There's also a walkable downtown filled with historic museums and fresh seafood to try, of course.
Lexington
Known as "The Birthplace of American Liberty," history is lurking in virtually every corner of Lexington—including Lexington Battle Green, where the first shot of the Revolutionary War was fired. The best way to explore is by booking a trolley tour: Your ticket allows you to jump on and off to take in the destinations at your own pace.
Wellfleet
Wellfleet is known for one of the world's most superior oyster harvests, which locals and visitors celebrate every October at the town's annual Oysterfest. Also not to be missed? The walkable downtown, lined with eclectic art galleries.
Cohasset
Situated just off of Boston's South Shore, Cohasset offers charming colonial-era architecture and scenic coastline views. Tour the Old Scituate Light House, wander into local boutiques on Hingham Square, and get pampered at Adamo Day Spa before sipping a cocktail at The Red Lion Tavern, which has been in business since 1704.
Deerfield
In Historic Deerfield, you'll find a preserved 330-year-old village full of old homes, vintage fashion boutiques, and antique furniture. Make time for Yankee Candle Village, which houses the brand's flagship store and offers interactive experiences and an on-site fudge shop, or take a short drive to the Magic Wings Butterfly Conservatory for family fun.
Osterville
This oceanfront town, located on the Cape, is celebrated for its fresh seafood. (In fact, it originally was called Oysterville until a typo changed the town's name forever!) Grab a bite to eat at Wimpy's Seafood Market before stopping by the Osterville Mercantile, a modern general store, for homemade chocolates.
Hingham
Just miles away from Boston proper sits Hingham, a nature respite from bustling city life. The town is home to World's End, a series of walking paths designed by legendary landscape architect Fredrick Law Olmsted, who notably designed Central Park and the grounds of the U.S. Capitol. Catch a glimpse of the Boston skyline from the park before exploring Weir Farm, a working farm with a full calendar of family-friendly activities.
Essex
Antiques lovers, this is the place for you! Essex is known as "America's Antique Capital," with dozens of shops offering everything from antique furniture to vintage art and décor. Once you've had your fill, try your hand at glassblowing at the Bubble Factory—a hands-on, fully operational studio set in an converted horse barn—or kick back on a river cruise.
Shelburne Falls
This nature-forward village sits on the Mohawk Trail, New England's first scenic road with top-tier views of the Berkshires. Stop by the Bridge of Flowers, where volunteers plant gardens on a retired trolley bridge, or head to Salmon Falls for a breathtaking peek at cascading falls and glacial potholes.
Pittsfield
Pittsfield might be the largest town in the Berkshires, but its small-town qualities make it a dreamy escape. Thanks to its burgeoning arts scene, there are plenty of year-round music, dance, and theater performances—and if visual arts are more your thing, North Street is home to dozens of galleries. Snow lovers, Bouquet Mountain is your spot!
New Bedford
Combining coastal vibes and history, New Bedford was once the whaling capital of the world when Herman Melville wrote Moby Dick and is still the number-one fishing port in the country. Visit the New Bedford Whaling Museum or hop on the ferry to experience Cuttyhunk, a nearby island with a floating shellfish raw bar. If you'd rather enjoy your seafood on land, try The Black Whale.
Concord
Just 20 miles outside of Boston, Concord is bursting with local charm and history. History buffs can retrace the steps of Revolutionary War soldiers on the Battle Road Trail, while book lovers can stop by Walden Pond and the Orchard House, the home that inspired Little Women.
Dennis
Located in the heart of Cape Cod, Dennis is a beach town divided into five adorable villages. Surfers will enjoy Mayflower Beach before indulging in an unforgettable waterfront dining experience at the Ocean House or aboard Sesuit Harbor Café's lobster roll cruise.
Harwich
While most of Cape Cod's villages deliver on the small-town promise, Harwich might be the coziest of the bunch! Main Street is a prime shopping destination with bookstores, candy shops, and boutiques full of local goods. Harwich also has several entry points to the Cape Cod Rail Trail, where visitors can bike down the 25-mile-long path to scope out the region's wildlife.
Brewster
There's no shortage of nature and sights in Brewster, home to the famous Brewster Flats tidal pools and the Old Higgins Farm Windmill. If you're traveling with kids, swing by the Cape Cod Museum of Natural History, home to an aquarium highlighting local sea creatures. Directly behind the museum, you'll find a nature trail that runs along Cape Cod Bay.
Foxborough
Home to the NFL's New England Patriots, this is where football fans can tour the Patriot Hall of Fame before grabbing a bite at one of Patriot Place's restaurants. If you're not a sports lover, there's still something for you here: historic buildings, a must-visit farmers market, and a seven-acre cranberry bog, to name a few.
Amherst
With the Emily Dickinson Museum, Mount Holyoke Range State Park, scenic Puffers Falls, the Amherst Farmers' Market, cute coffee shops, and more, Amherst is certainly more than a college town. But its college campuses have attractions of their own: Amherst College houses one of the largest natural history museums in New England!
You Might Also Like
