The Most Picturesque Small Towns In Massachusetts
It is going to be a tough call picking out the most picturesque small towns in Massachusetts. This is regardless of whether one focuses on the Boston area and the state’s shoreline, where small towns spot tasty waterfronts and heart-melting Colonial architecture — or the western side, particularly the Berkshires — a well-known leaf-peeper’s paradise. That said, the list of the most picturesque towns has both big names, such as Provincetown, and a few surprises. Starting with Northampton, discover below the most picturesque small towns in the Bay State.
Northampton
One of the most picturesque small towns in Massachusetts is secreted in the fertile Pioneer Valley, less than 30 minutes from Springfield, the third largest city in Massachusetts. Northampton is encircled by verdant farmland, traversed by the Connecticut River, and bordered by a galaxy of excellent schools — the prestigious Five College Consortium. Art lovers can rouse their senses at spots such as Smith College Museum of Art, whose exceptional collection includes some of the world’s finest, including Picasso and Monet. Catch a show at the Academy of Music located right on Main Street, then proceed to the Haymarket Cafe a few steps away to wash down an afternoon with smoothies and other healthy treats. Just so you don’t overlook it, the Academy of Music is the oldest municipally-owned theater in the United States.
Newburyport
Newburyport is a quaint historic town with a relaxing atmosphere, chic boutiques, tasty restaurants, and a nautical vibe and charm. Revitalization efforts in the town have enhanced its look and appeal, particularly its historic architecture and lovely, waterfront setting. Custom House Maritime Museum, now serving as the portal to the town’s maritime history, is an architectural masterpiece. It is the brainwork of Robert Mills, the architect of the iconic Washington Monument. Kickstart your adventure at Brown Sugar by the Sea, a charming neighborhood joint doling out traditional Thai cuisine in a bright and bubbly space. If you are into seafood, however, Sea Level Oyster Bar, which fronts the Waterfront Promenade Park, is the place to be. On the outdoorsy side, Parker River National Wildlife Refuge Gatehouse, just a hair out of town, is a great place to walk and enjoy top-tier bird watching year-round.
Rockport
If there is a Massachusetts town that looks plucked straight out of a fairy tale, it has to be Rockport, a lovely eye candy located about 40 miles from Boston. A first-time visitor can just chill in town — slowly taking in its vibe and look — or venture out to the dog-friendly Halibut Point Park, just three miles from downtown Rockport. Halibut offers great views of the ocean, easy walking trails, an amazing granite quarry, and tide pools. Back in town? Get some fresh lobster rolls from Roy Moore Lobster Company. The rolls here are often packed with tender lobster meat, while the bread is buttery, soft, and delicious. Still on Main Street, view beautiful artwork at the Rockport Art Association & Museum before getting Salt Water Taffy or some lobster-shaped lollipops at Tuck's, just across the street from the museum.
Salem
Don’t get your hair raised. You will not find any witches in Salem — even if the town itself is hauntingly beautiful, especially outside of tourist season. Think of a diverse coastline, a fun downtown area, cute restaurants, and, of course, the Salem Willows Arcade and Park, an oceanfront park named for the European white willow trees planted there more than two hundred years ago to form a shaded walk for patients recuperating at a nearby smallpox hospital. Then again, it would be a mistake to miss Winter Island, including Waikiki Beach, a fantastic place to get wet, enjoy a walk, or sightsee. Back in town, Chestnut Street, with its graceful architecture and trees, has been called the most beautiful street in the United States. That said, do not miss the House of the Seven Gables on Derby Street, which served as the setting of Nathaniel Hawthorne’s 1851 heart-gripping masterpiece.
Lenox
Many people know Massachusetts as a space that revolves around Boston and the stretch along the coast. Newsflash: The most beautiful part of Massachusetts is in the Berkshires, especially if natural beauty counts for something. The eyes here are swayed by beautiful mountain views, the bright smile of flowers (especially in fall), and heart-stirring views, almost yard after yard. In the public mind, Lenox is mostly associated with Tanglewood, the summer home of the Boston Symphony Orchestra, one of the oldest American symphony orchestras, with a history that goes back to 1881. Nature, however, takes center stage at Pleasant Valley Wildlife Sanctuary, set along the slopes of Lenox Mountain. Still, do not overlook Kennedy Park, especially for its scenic trails, Mount Edith Wharton’s Home, if just to peer into the rooms where the Pulitzer Prize-winning author once lived, and Brava, especially if good wine is up your alley.
Provincetown
From Belgium to Brazil, Provincetown is famous as the first landing site of the Mayflower in 1620. It is, therefore, connected to notions of freedom, conviction, and courage. Although much has changed, with the town transforming itself into a gay paradise, its allure is undimmed. Whether one wants to enjoy the gentle waves of Herring Cove Beach — or the more agitated ones at Race Point Beach — any type of beach bum will come out gratified. That said, if you did not get the memo, Provincetown is the oldest continuous artist colony in the entire country. So if you want to fire your imagination, and love modern art, check out the Provincetown Art Association and Museum. Alternatively, just spend some time ambling through the town’s Gallery District, which is home to over 40 galleries. There is the Pilgrim Monument, the tallest granite structure in the United States, and the on-site museum, which houses a diorama of the signing of the Mayflower Compact.
Plymouth
Think of a tasty waterfront. But not just that. A walkable downtown area. Then there is the Nelson Memorial Park, with its pretty beach and splash pad, the National Monument to the Forefathers, both an exceptional work of art and an amazing piece of history — and the criminally overlooked Plimoth Grist Mill, a reconstruction of the first mill built by the Pilgrims in Plymouth Colony nearly four hundred years ago on the same site. Enjoy the lush, heart-warming greenery of the Brewster Gardens as you take a leisurely stroll back to town in settings that are cool and tranquil. And with its tons of new bars, restaurants, and stores, including The Black Dog on Main Street, which set shop in May 2024 — Plymouth has a lot to offer.
Hudson
Hudson boasts a fabulous Main Street, which is pleasant and walkable and has an overall look that is among the most swoon-worthy of any Massachusetts small town. The Assabet River flows through the town, adding a layer of rustic charm to an already beautiful spot. No one will want to miss the New City Microcreamery, especially if you want to enjoy Hudson one scoop at a time. No wonder they have been voted the best ice cream in Massachusetts. If you want to experience a WWII battle reenactment, complete with one of the most impressive collections of military vehicles used in the war, the American Heritage Museum simply has no competitor. That said, if you are a social butterfly and looking for a place to chill or chat up locals, Horse Shoe Pub is a homey, family-run establishment, loved for its expansive beer list and patio seating.
Shelburne Falls
If someone staged a contest-themed “the most beautiful rural town in Massachusetts,” Shelburne Falls would take the hardly-fought-for crown. So, what sets this paint-worthy town apart? It is a look you have never seen elsewhere — or seen at a few other spots. One can start by grabbing the ultimate New England fall foliage photo-op along the Bridge of Flowers, touted as “the only one of its kind in the world.” This narrow but breathtaking walkway offers beautiful vistas of the surrounding hills — and is among the town’s most defining landmarks. Shelburne Falls Potholes, right around the corner from the iconic Bridge of Flowers, is a nice, whimsical landscape with whirling pools left behind from the Glacial Age. A hearty meal at Foxtown Diner, a cash-only establishment that locals love to bits — should prime one for the adventure. Alternatively, West End Pub, conveniently close to the bridge, comes with beautiful views of the water. If you want to break some sweat and looking for something heart-pounding, Shelburne Firetower Trailhead easily fits the bill.
The Takeaway
Only a few states in the country can hold a candle to Massachusetts, especially when it comes to its rich colonial history, spellbinding shoreline, and heart-stirring natural beauty. Small-town tourists will enjoy ambling through cobblestoned streets, marveling at old, red-brick buildings, and sampling the state’s electrifying art scene. Although picking the most picturesque small towns in Massachusetts can be a pretty difficult affair, the competitive line-up cannot miss treasures such as Northampton, Provincetown, and Shelburne Falls, arguably the most beautiful rural town in the state.
