9 Picturesque Small Towns in Massachusetts for a Weekend Retreat

While Massachusetts is home to Boston, one of the most beautiful cities in the world, its small-town offerings are just as impressive. Whether you're looking to explore the Bay State’s picturesque coastline and marvel at elegant, Colonial-era mansions and sites, or venture westward to the Berkshires for some of nature's most breathtaking sceneries, Massachusetts often exceeds expectations. However, for smaller and quainter spots, discover below nine picturesque small towns in Massachusetts. Needless to say, each of these can make for an amazing weekend retreat.

Saugus

For starters, Saugus is just about 10 miles from downtown Boston, so you don't have to spend a whole day driving, arrive tired, and immediately collapse in bed. It packs a punch. For instance, even if you're particular about its food, standard Chinese American fare, or drinks, the famous Kowloon Restaurant is worth checking out. It could be for the history or the top-notch decor and atmosphere. Kowloon Restaurant, more than 70 years old, is arguably the largest Chinese restaurant in New England. It will transport your mind back to the time when quirky restaurants dominated Route 1 and to the period when it was New England’s go-to spot for scorpion bowls. But Saugus is home to other attractions as well. Breakheart Reservation, with its hardwood forest, freshwater lakes, and stunning Boston views, can easily fill a weekend. Then there's the 65-acre Camp Nihan (ideal for group camping), Rumney Marsh, an excellent fishing and boating venue, and the Saugus Iron Works Historic Site, a reconstruction of the first successful integrated ironworks in the Americas.

North Adams

It is a bit of a drive from Boston, taking about two and a half hours, but North Adams provides a weekend getaway experience that is hard to rival. You'll want to make a detour to the Golden Eagle Restaurant, a culinary gateway to North Adams for well over a century. Known to offer delicious treats for weary travelers, the Golden Eagle Restaurant offers even more breathtaking views, especially of the hilly and winding Mount Greylock area. The Mohawk Trail, featuring more than 60 miles of unsurpassed splendor, provides a dreamy, trance-like welcome to North Adams and is worth exploring. Once in town, enjoy a hearty breakfast at Renee's Diner before checking out the masterpiece that is the Massachusetts Museum of Contemporary Art. After this, a quick and affordable lunch awaits at the 107-year-old Jack's Hot Dog Stand. For your afternoon or evening, The Cascades spans 85 acres and features scenic hiking trails as well as a lovely 45-foot waterfall.

Rockport

Back on the North Shore, Rockport, which is less than an hour’s drive from Boston, is just as impressive and worth checking out. Halibut Point State Park, a beautiful expanse of granite between the ocean and the mainland, offers stunning ocean views and features multiple hiking trails. You will also enjoy wandering through Bear Skin Neck, especially when hunger pangs start to kick in. This quaint shopping area is brimming with art galleries, candy shops, and casual but classy restaurants. Some exceptional clam chowder at My Place by the Sea, for instance, may come in handy. This restaurant, while fairly small, is right next to the water and is ideal, especially if you want to feel the cool, refreshing ocean breeze. Alternatively, for an out-of-this-world cocktail sauce, The Lobster Pool, which is conveniently close to Halibut Point State Park, may suffice. And then there are the beaches.

Gloucester

While you can combine a visit to Rockport and Gloucester to maximize your weekend experience, you may want to explore these two destinations separately for a fuller appreciation of each. Gloucester, of course, is larger, home to about 29,700 residents. Attractions in the area include Dogtown, a ghost town with an intriguing story that has become the stuff of legend. Once settled in 1693 by farmers keen to protect themselves from the threat of pirates along the coast, this settlement was completely abandoned by the first half of the 19th century. However, they left their dogs behind, hence the enduring name. Much later, an eccentric Massachusetts Institute of Technology-trained engineer hired unemployed quarry workers to carve thought-provoking words into the boulders scattered around the area. You will find inscriptions such as “Stay out of Debt,” “Help Mother,” and “Be on Time.” For those looking to dip their toes in the water, Pavilion Beach is nearby. Nonetheless, no matter how pressed for time you are, you cannot skip Stage Fort Park, the historic site of Gloucester's first settlers.

Brimfield

Brimfield, just 66 miles from Boston, is a little over an hour's drive away but offers a significant experience. It is known as the Antique and Collectibles Capital of the United States. The Brimfield Antique Flea Market is reputed to be the oldest outdoor antiques flea market in America. This week-long event, held three times a year, is known to attract thousands of collectors and dealers from around the world. In 2024, the flea market will run from May 14-19, July 9-14, and September 3-8. Visitors can expect to find a lifetime's worth of antiques and items rarely seen elsewhere. For those looking to engage in physical activity or simply enjoy some fresh air, the picturesque Brimfield Bike Trail is a must-visit. Additionally, Old Sturbridge Village provides an awe-inspiring recreation of a 1830s rural New England town, capable of captivating visitors for an entire morning.

Williamstown

Exploring the entire Berkshires in a weekend is a challenge. Combining North Adams and Williamstown for an extended trip is an option, but if time is limited, choosing one over the other may be necessary. Nestled along the picturesque Hoosic River, about 21 miles north of Pittsfield, Williamstown is a vibrant college town and home to Williams College. Founded in 1793, Williams College is consistently ranked as the best liberal arts college in the nation. Cricket Creek Farm, located on the slopes of the Taconic hills, offers artisanal farmstead cheeses, delicious raw milk, and a nice selection of frozen grass-fed beef, making it a worthwhile stop, especially for those exploring the Taconic Trail State Park. The Williamstown Theatre Festival is a summer event that attracts some of the finest actors to the Berkshires for thrilling, fun-filled performances. The Clark Art Institute, one of the town’s defining attractions, houses captivating works from various artists, including Monet, an influential figure in the Impressionist movement, and Remington, celebrated for his paintings of the old American West. Additionally, the area boasts scenic hiking spots, including the March Cataract Falls Trail, the Appalachian Trail, and numerous trails at the Mount Greylock State Reservation Area.

Hyannis

The Mid-Cape region offers a rewarding weekend retreat with its abundance of restaurants and outdoor adventure venues. Hyannis, the largest recreational boating port on Cape Cod, is particularly noteworthy. This town is closely associated with the Kennedys. It was here that the 35th president, known for his leadership during the Cuban Missile Crisis, would come to relax, celebrate, or grieve. While the Kennedy property itself is not accessible to the public, a view from a close range is still worth the trip. The town's harbor area is also a notable attraction. For beach enthusiasts, Craigville Beach, one of the largest in the Mid-Cape area, is renowned for its magical sunsets. Additionally, the John F. Kennedy Hyannis Museum offers a glimpse into the life of one of America’s most beloved presidents, providing a moving and informative experience. The Melody Tent, with its rotating stage, attracts visitors from across New England, offering a variety of shows. Hyannis also serves as an affordable base for exploring other attractions along this stretch of the Cape, including Yarmouth and Dennis.

Edgartown

Martha’s Vineyard, home to Edgartown, boasts some of the most beautiful beaches on the East Coast and offers a fantastic weekend getaway. Edgartown, the oldest settlement on the island with nearly 400 years of history, exudes Old World charm despite its luxurious and affluent atmosphere. One notable resident is President Barack Obama, whose seven-bedroom house is set on nearly 30 secluded acres. Visitors will enjoy exploring the island's attractions, such as the Martha’s Vineyard Museum, which houses fascinating artifacts from the shipbuilding era. Morning Glory Farm, offering locally sourced fresh produce and baked goods, is another must-visit. Additionally, visitors can climb the Edgartown Harbor Lighthouse or explore the nearby sandy beach.

Northampton

Located along the Connecticut River, approximately 17 miles northwest of Springfield in west-central Massachusetts, Northampton is rich in both indoor and outdoor attractions. Look Memorial Park, spanning over 150 acres, features peaceful picnic areas shaded by large trees. In spring, guests can enjoy a mile-long ride on an authentic replica of the 1863 C.P. Huntington Train. The Academy of Music Theatre, the first municipally-owned theater in the U.S. and the only one to have shown films for three consecutive centuries, is known for its excellent visuals and acoustics. History enthusiasts will appreciate the Calvin Coolidge Presidential Library & Museum, located on the second floor of Forbes Library, which highlights the life of the 30th president, perhaps the town's most famous resident. Outdoor activities include paddling down the river and catching sunsets at Skinner State Park.

The Takeaway

Swap your suit for flip-flops and casual wear to enjoy the delightful small-town charm of Massachusetts. As the home state of the Pilgrims, the Mayflower, and the Boston Tea Party, Massachusetts offers a rich tapestry of history and beauty. From Saugus, Boston’s neighbor, to North Adams and Williamstown in the stunning Berkshires, Massachusetts' picturesque small towns offer diverse styles and settings. The list of picturesque small towns in the Bay State would not be complete without mentioning gems such as Rockport, Gloucester, and Edgartown.