10 Nicest Small Towns In Massachusetts
The small towns of Massachusetts spread across landscapes surrounded by early American history. The towns along Cape Cod Bay offer the best seafood, like the fresh oysters from Wellfleet. Further inland, you can relive the American Revolution in towns like Concord and Lexington where bike and walking trails connect you directly with history. And you can experience the natural beauty of the Berkshires hiking the mountain trails of Jug End State Reservation in Egremont or the landscaped gardens of Chesterwood in Stockbridge. These towns are some of the nicest Massachusetts has to offer.
Wellfleet
Located on the eastern end of Cape Cod, Wellfleet has the perfect mix of access to the natural beauty of Cape Cod, historical significance, and a small, walkable downtown perfect for shopping or for grabbing something to eat. By the 1650s, Wellfleet's rich fish stocks attracted its first permanent settlement. However, by the end of the 19th century, commercial fish began to decline. The natural beauty of the area was preserved in 1961 with the establishment of the Cape Cod National Seashore, including 8,000 acres of the town. Today you can explore much of this wild land with some of the best seaside hikes and scenic views overlooking Cape Cod Bay. The Great Island Trail includes 3.9 to 8.8 miles of hiking through marsh, sandy dunes, and bay-side beaches. Along the route is an old tavern site. The original tavern dates to between 1690 and 1740. If you are looking for more history, the Wellfleet Historical Society and Museum shares the story of Wellfleet through exhibitions and walking tours. If you ever wondered where you can find the best oysters on Cape Cod, look no further than Winslow's Tavern. The raw bar is stocked with local shellfish shucked to order. Grab one of the outdoor tables overlooking the shops on Main Street, or head upstairs for a craft cocktail at the main bar. With so much history, natural beauty, and the compact Main Street, Wellfleet is truly one of the nicest towns in Massachusetts.
Edgartown
Just south of the Cape on Martha's Vineyard, Edgartown is surrounded by scenic ocean vistas and a beautiful natural environment. This town is so scenic, the nearby beaches served as the film locations for the original Jaws film. Despite the frightening depictions, the film highlighted the island's allure. Edgartown also has seasonal ferry access to Falmouth, and a protected harbor. The Edgartown Harbormaster offers nightly mooring rates, or you can charter a catboat. Catboat Charters offers private outings on the historic craft. These wide sailing boats once served as fishing and light cargo boats in the waters between the Cape and Islands. A great way to explore the town is on foot. The Vineyard Preservation Trust offers walking tours starting from the Old Whaling Church. Or for an easily accessible hike, check out the Edgartown Lighthouse Walk. The original lighthouse dates to 1828 and the walkway quickly became a popular evening activity. When a rock breakwater was added to protect the bridge, sand began accumulating creating an island that now surrounds the lighthouse, including a sandy lighthouse beach. And to cap off your hike, the lighthouse is available for tours as well. If you're wondering where to get the best whole boiled lobster on Martha's Vineyard, look no further than the Seafood Shanty. The harborside, casual restaurant has a rooftop deck and serves up whole steamed lobsters with drawn butter and claims to have the island's largest lobster roll.
Duxbury
Moving onto the mainland, Duxbury sits on the shores of Cape Cod Bay, 35 miles south of Boston. The early Pilgrims arrived at Plymouth in 1620 and spread northward after receiving their land grant. Duxbury, or Duxborough as it was known then, grew into a farming village. By the 19th century though, summer visitors out of Boston began arriving. Ever since its been a recreational destination. Duxbury Beach Park offers accessible, sandy swimming beaches extending from Marshfield into the bay toward the private island of Saquish Head. The family-friendly beach offers daily parking. The Duxbury Rural & Historical Society maintains several historic buildings around town, including the Nathaniel Winsor Jr. House and the Drew Archival Library that are opened year-round. Other buildings in their collection are opened seasonally or for special events. The Winsor House At Island Creek Oyster Farm offers a menu filled with shellfish like oysters, and scallops. The restaurant occupies a historic tavern and is just across the street from the Island Creek's oyster farm ensuring a fresh, steady supply of bivalves. And if you are looking to grab a local gift, check out Duxbury Supply Co. The store is filled with beautifully designed glassware, home decor, antiques, furniture, and textiles.
Rockport
Jutting out between Massachusetts Bay and Ipswich Bay, Rockport sits on the eastern end of Cape Ann. Originally part of Gloucester, the town began life as a dock for shipping timber in the 1740s. It remained part of Gloucester until 1840. The historic houses add to the charm of Rockport's downtown. The Sandy Bay Historical Society resides in one, the Sewall-Scripture House. Constructed in 1832, the Federal Style building serves as the society's museum. The society also maintains the Old Castle, an 18th century wooden farmhouse. The coastline along much of Rockport consists of stony shorelines leading into the sea. Swimmers can find a sandy place to access the water at Front Beach. In season the beach has lifeguards to protect swimmers. Part of what makes Rockport such a nice small town is the lively arts community. Main Street is lined with art galleries, and right in the downtown you will find the Rockport Art Association & Museum. The organization celebrates the 150-year history of artists coming to Cape Ann for beautiful seascapes and the unique natural beauty of the rock coast. The museum hosts rotating exhibitions and association members' works. The museum also provides exhibits like sketching with colored pencils, experimenting with gel plates, and teen arts workshops. And with a working fishing port, there's no better place to grab one of the best New England clam chowders in Massachusetts. The Roy Moore Lobster Company has chowder, lobster rolls, fish cakes and house-smoked seafood.
Wellesley
The beauty and convenience of the colonial-era town of Wellesley has long attracted the business elite. Today, there are direct commuter trains to Boston from several stations in town. But the appeal was evident as early as the 19th century. In the 1870s, businessman Henry Durant and his wife Pauline founded Wellesley College, one of the Seven Sisters. The college campus exploits the scenic beauty of the area with the campus sprawling alongside several lakes. The college provides a great amenity for the town, such as the Whitin Observatory. First built in 1900, the complex has been expanded and modernized several times. The A.S.T.R.O. Club hosts free public nights allowing locals the opportunity to gaze into the stars. Outdoor recreation plays a big part in making Wellesley one of the nicest towns in Massachusetts. There are more than 48 miles of trails connecting the town's greenspaces and conserved parcels of land. The Wellesley Trails Committee also hosts free guided tours of the paths. Another reason Wellesley is one of the nicest towns in Massachusetts is the walkable downtown. Here you will find plenty of independent shops like Henry Bear's Park, a children's toy store. Inside you will find BRIO wooden trains, dolls like Barbie and Calico Critters animals, and plenty of seasonal gear like a Bluey inflatable sprinkler.
Lexington
Northwest of Boston, Lexington's link to American Revolutionary history plays a big part of this historic town's charm. Best known for its role in the opening battle of the American Revolution, the town lays claim to being "The Birthplace of American Liberty." The Lexington History Museums, formerly the Lexington Historical Society, date back to 1886. The museums oversee a collection of historic buildings including the Buckman Tavern where the militia gathered in April of 1775 to await the arrival of the British. The museums also host special exhibitions on rotation, and a permanent exhibition in Hancock-Clarke House. Part of what makes Lexington a nice small town is the lively, pedestrian-friendly downtown. Here you will find great local independent businesses like the Nouvé Bakery. The shop features an assortment of delicate French-style pastries and baked goods. If pastries are not enough to satisfy your sweet tooth, check out Liberty Sweets just down the street. The shop offers fudge, bulk candy, and locally made fine chocolates. Lexington also has 26 conservation areas with more than 50 miles of trails. Many of these local walking and hiking trails connect to the Minuteman Bikeway. The bike and mixed used rail-to-trail path runs directly through the heart of Lexington. The path links the Alewife T station in Cambridge to Bedford, Massachusetts and passes by the Buckman Tavern and the Lexington Battlegreen. The trail is a great way to connect with the history in this small town.
Concord
Just a few miles to the west, Concord provides a combination of history and natural beauty. At the edge of town is a replica of the North Bridge. At the start of the American Revolution, this critical water crossing saw the first shots fired, known colloquially as the "shot heard 'round the world." The conflict at the bridge began the 16-mile battle between British Redcoats and American Colonial Militia as the British army marched back to Boston. Today the National Park Service has a visitor center and a brass cannon, one of four smuggled out of Boston and hidden in Concord. You can also walk or bike to Concord on the 4-mile Reformatory Branch Rail Trail. The dirt path connects to historic Bedford, where you can also connect to Lexington on the Minuteman Bikeway. Concord also features a small downtown shopping district. An essential stop is The Concord Bookshop. Founded in 1940, the general interest bookstore offers new releases, signed books, and a large selection of children's books. And Walden Street provides a great opportunity for antiquing with three distinct shops all adjacent to each other. North Bridge Antiques, Walden Street Antiques, and Thoreauly Antiques make this a must-stop for history collectors.
Uxbridge
Located in central Massachusetts, Uxbridge sits in the center of the Blackstone Valley. The valley played an integral role in the industrial revolution. The manmade Blackstone Canal linked Worcester, Massachusetts with Providence, Rhode Island, providing a vital link to transport manufactured goods at the dawn of the industrial age. Today, the Blackstone River and Canal Heritage State Park includes 1,000 acres of natural parkland for hiking, biking, horseback riding, and even canoe access. River Bend Farm Visitor Center recalls the era of canal transportation when raw materials and manufactured goods transited through Uxbridge. Inside the barn are exhibits showcasing the local history. Along the Uxbridge Common, Honeysuckle Roastery and Cafe serves up house-roasted beans in a variety of espresso drinks. The pastries here are baked fresh daily, and you will find hot and cold sandwiches for breakfast and lunch. The cafe is just around the corner from the Falls on the Mumford River, sometimes called the Capron Falls. The falls once provided power to Uxbridge's industrial past. Today, the scenic river view can be seen from the bridge on Mendon Street.
Egremont
Continuing west into the Berkshires, Egremont sits on the New York State border. The town's history weaves through the scenic natural beauty of the mountains. During the Revolutionary War, General Henry Knox carried artillery through North Egremont on the way to Boston. Following the capture of Fort Ticonderoga, Knox led the captured equipment on the 300-mile journey to Boston where the equipment forced the British to evacuate the city. Today you can find the General Henry Knox Cannon Trail Marker in North Egremont, and follow in his path along the existing road network. You can also find some of the best scenic views in the Berkshires in Egremont. Jug End State Reservation & Wildlife Management Area consists of 1,158 acres of preserved woodlands and mountain overlooks. There's also great hiking in the preserve. The Jug End Loop Trail follows the ridge line overlooking the Berkshires, and there's access to the Appalachian Trail and Mount Everett, the highest peak in the southern Taconic Mountains. To keep yourself provisioned in this rural community, stop by the Old Egremont Country Store where you will find locally made products like maple syrup and deli sandwiches for picnicking in the scenic mountains.
Stockbridge
British missionaries settled Stockbridge in 1737 and the town incorporated two years later. The historic town sits on the Housatonic River in the heart of the Berkshires. Historic homes line the quiet streets of this small town. The town embodies traditional Americana, and that's no accident. The reason the town looks and feels like a Norman Rockwell painting is because the painter lived there for many years. Rockwell drew inspiration for his classic paintings from the town and the people living there. The Norman Rockwell Museum celebrates the artist's work and highlights his connection to the town in their exhibits. The rotating exhibits include more than Rockwell's paintings, drawing on the themes in his body of work to craft broader narratives. You can also see the natural beauty of the region on the grounds of the nearby Chesterwood, the home of sculptor Daniel Chester French. Now operated by the National Trust for Historic Preservation, the roughly 130-acre compound includes gardens and woodlands with pathways for walking. Inside you will find antiques and vintage furniture. French sculpted The Minute Man, a statue based in Concord commemorating a farmer joining the patriot militia. The downtown includes shops and boutiques. Check out Whispered The Heart, an independently owned gift store offering local artisan crafts like pottery, woodworking, glassware, and mixed-media sculpture. As for small towns, few are as nice as the postcard-worthy Stockbridge.
Nice Small Towns Connect With Nature and History
These nice small towns in Massachusetts have integrated their history into their communities through parks and trails. Whether you want to see artistic interpretation of natural beauty in local museums and galleries, or experience it in-person hiking mountain trails, you can find the activity that best suits you in these small towns.
