Massachusetts is home to one of the world’s most beautiful cities, Boston, but its small-town charm is just as impressive. If you want to explore the Bay State’s picturesque coastline and marvel at elegant colonial mansions and ruins, or venture west into the Berkshires for some of nature’s most breathtaking views But Massachusetts often exceeds expectations. But for smaller, more quaint spots, check out these nine picturesque small towns in Massachusetts. Needless to say, any of these would make for a great weekend retreat.
Saugus
First, Saugus is only about 10 miles from downtown Boston, so you don’t have to arrive tired from a full day’s drive and then immediately collapse into bed. It packs a punch. For example, whether you’re picky about food, standard Chinese-American fare, or drinks, the famous Kowloon Restaurant is worth checking out. It may be because of the history, or it may be because of the top-notch decor and atmosphere. Kowloon Restaurant has been in business for over 70 years and is probably New England’s largest Chinese restaurant. It transports your mind back to the days when quirky restaurants dominated Route 1 and when Scorpion was New England’s favorite bowl spot. But Saugus has other attractions as well. With hardwood forests, freshwater lakes, and stunning views of Boston, weekends fill up quickly at Breakhart’s Reservation. Additionally, there’s the 65-acre Camp Nihan (perfect for group camping), Rumney’s Marsh, perfect for fishing and boating, and the Saugus Steel Mill Historic Site, which rebuilt the first successful integrated steel mill in the Americas.
north adams
Although it’s a bit far, about a 2.5-hour drive from Boston, North Adams offers a weekend getaway experience like no other. Take a detour to Golden Eagle Restaurant, a culinary gateway to North Adams for more than a century. Known for providing delicious treats for weary travelers, the Golden Eagle Restaurant offers even more spectacular views of the particularly hilly and winding Mount Greylock area. Featuring over 90 miles of unparalleled splendor, the Mohawk Trail offers a dream-like, trance-like welcome to North Adams and is well worth exploring. Once in town, enjoy a hearty breakfast at Lenny’s Diner, then admire the masterpiece Massachusetts Museum of Contemporary Art. Afterwards, enjoy a quick and affordable lunch at the 107-year-old Jack’s Hot Dog Stand. Perfect for an afternoon or evening, the 85-acre cascade features beautiful hiking trails and a stunning 45-foot waterfall.
lock port
Back on the North Shore, Lockport, less than an hour’s drive from Boston, is equally impressive and worth checking out. Halibut Point State Park is a beautiful stretch of granite rock between the ocean and the mainland, offering stunning ocean views and multiple hiking trails. Strolling around Bear Skin Neck is fun, especially when the hunger pangs start to hit. This quaint shopping area is filled with art galleries, candy shops, and casual but upscale restaurants. For example, My Place by the Sea’s exceptional clam chowder may come in handy. This restaurant is quite small, but it’s right next to the water, which is great, especially if you want to feel the cool, refreshing sea breeze. Or, if you’re looking for an out-of-this-world cocktail sauce, the lobster pool, conveniently located near Halibut Point State Park, might be just the ticket. And there’s also a beach.
gloucester
While you can combine Lockport and Gloucester to get the most out of your weekend experience, you can also explore these two destinations separately to get a deeper taste of each. Gloucester is, of course, larger, with about 29,700 residents. Attractions in the area include Dogtown, a ghost town with an interesting story that has become legendary. Once settled in 1693 by farmers eager to protect themselves from the threat of pirates along the coast, the settlement was completely abandoned by the first half of the 19th century. But they left the dog behind, so the name stuck. Much later, an eccentric Massachusetts Institute of Technology-trained engineer hired unemployed quarry workers to carve thought-provoking sayings into the rocks that dotted the area. You will find inscriptions such as “Do not go into debt”, “Help your mother”, “Be punctual”, etc. Nearby is Pavilion Beach, where you can enjoy swimming. Nevertheless, no matter how short on time you are, you can’t skip Stage Fort Park, a historic site of Gloucester’s first settlers.
brim field
Just 106 miles from Boston, Brimfield is just over an hour’s drive away, but offers a unique experience. Known as the antique and collectibles capital of the United States. Brimfield Antique Flea Market is known as America’s oldest outdoor antique flea market. Held three times a year, his week-long event is known for attracting thousands of collectors and dealers from all over the world. The 2024 flea market will be held from May 14th to 19th, July 9th to 14th, and September 3rd to 8th. Visitors can expect to find a lifetime’s worth of antiques and items rarely seen elsewhere. For those looking to get some physical activity or simply enjoy some fresh air, the picturesque Brimfield Bike Trail is a must-see. Additionally, Old Sturbridge Village is a majestic recreation of an 1830s New England country town that will captivate visitors all morning long.
williamstown
It’s hard to explore all of Berkshire in a weekend. You can combine North Adams and Williamstown for a longer trip, but if you have limited time, you may need to choose one or the other. Located about 34 miles north of Pittsfield on the picturesque Hoosick River, Williamstown is a vibrant college town that is home to Williams College. Founded in 1793, Williams College is consistently ranked as one of the nation’s best liberal arts colleges. Located on the slopes of the Taconic Hills, Cricket Creek Farm offers artisan farm cheeses, delicious raw milk, and carefully selected frozen grass-fed beef, making it a worthwhile stop, especially for those exploring Taconic Trail State Park. is. The Williamstown Theater Festival is a summer event that brings the best actors to the Berkshires for thrilling and entertaining performances. One of the town’s signature attractions, the Clark Art Museum features fascinating works by a variety of artists, including Monet, an influential figure of the Impressionist movement, and Remington, famous for his paintings of the old American West. It has a collection of works. Additionally, the area is home to scenic hiking spots, including the March Cataract Falls Trail, the Appalachian Trail, and the numerous trails in Mount Greylock State Reserve.
Hyannis
The Mid-Cape region is full of restaurants and outdoor adventure venues, making for a rewarding weekend getaway. Hyannis, Cape Cod’s largest recreational boating port, is especially noteworthy. This town has deep ties to the Kennedy family. It was here that the 35th president, known for his leadership during the Cuban Missile Crisis, came to relax, celebrate, or grieve. The Kennedy House itself is not open to the public, but the view from up close is worth a visit. The town’s port area is also a notable tourist attraction. For beach lovers, Craigville Beach, one of the largest beaches in the Mid-Cape region, is famous for its magical sunsets. In addition, John F. Kennedy’s Hyannis Museum provides a moving and informative experience, offering a glimpse into the life of one of America’s most beloved presidents. Melody’s tent, with its rotating stage, attracts visitors from all over England and hosts a variety of shows. Hyannis also serves as an affordable base for exploring other attractions along this stretch of the Cape, such as Yarmouth and Dennis.
edgartown
Home to Edgartown, Martha’s Vineyard boasts some of the most beautiful beaches on the East Coast and offers a great weekend getaway. At nearly 400 years old, Edgartown is the island’s oldest settlement, and despite its luxurious and affluent atmosphere, it oozes old-world charm. One notable resident is President Barack Obama, whose seven-bedroom home sits on about 30 secluded acres. Visitors will enjoy exploring the island’s attractions, including the Martha’s Vineyard Museum, which houses fascinating artifacts from the shipbuilding era. Be sure to visit Morning Glory Farm for fresh, locally sourced produce and baked goods. Additionally, you can climb the Edgartown Harbor Lighthouse or explore the nearby sandy beaches.
northampton
Located along the Connecticut River approximately 27 miles northwest of Springfield in central-western Massachusetts, Northampton is rich in both indoor and outdoor attractions. Spanning more than 150 acres, Rook Memorial Park offers a tranquil picnic area shaded by large trees. In the spring, he will enjoy a one-mile drive aboard an authentic replica of his 1863 CP Huntington train. The Academy of Music Theater was the first municipal theater in the United States, the only theater to have shown movies continuously for three centuries, and is known for its excellent visual and sound quality. History buffs will love the Calvin Coolidge Presidential Library and Museum, located on the second floor of the Forbes Library. It focuses on the life of perhaps the city’s most famous resident, the 30th president. Outdoor activities include river rafting and watching the sunset at Skinner State Park.
Take-out
Swap your suit for flip-flops and casual wear and enjoy Massachusetts’ fun small-town charm. Home to the Pilgrims, the Mayflower, and the Boston Tea Party, Massachusetts offers a rich tapestry of history and beauty. From Boston’s neighboring town of Saugus to the picturesque Berkshires of North Adams and Williamstown, Massachusetts’ picturesque small towns offer a variety of styles and environments. No list of the Bay State’s picturesque small towns would be complete without mentioning gems like Lockport, Gloucester, and Edgartown.
