8 Unforgettable Small Towns to Visit in Massachusetts

Between its Revolutionary War roots, wonderful Cape Cod beaches, and fresh seafood from the Atlantic Ocean, Massachusetts delivers a lineup of exciting tourist experiences throughout the year. While there is no question that almost half of the over 50 million tourists in the state in 2024 chose Boston as their vacation destination, there are many other fantastic places that guests can choose instead.

From the coastal lowlands and the lush Berkshires to the Connecticut River Valley, visitors have a full itinerary of activities to indulge in. Whether you plan to hike through the rolling landscapes of the Berkshires in Great Barrington or explore the immersive folklore of the 17th-century witch trials in Salem, here are some of the most unforgettable small towns to visit in Massachusetts.

Gloucester

Gloucester is home to the oldest seaport in the United States. It is steeped in rich maritime history and coastal beauty, welcoming guests to immerse themselves in the region's nautical heritage at Maritime Gloucester. This working waterfront boasts a variety of hands-on exhibits, including a functional marine railway, vintage sailing schooners, and a seasonal Seapocket Aquarium. Tourists enjoy ready access to the beautiful coast at Good Harbor Beach. This serene Atlantic Ocean beach is popular for its expansive white sand shoreline surrounded by beautiful dunes, which offer great strolling opportunities at low tide and provide ideal conditions for surfing during high tide.

Visitors have a rare opportunity to spot the region's marine life courtesy of the Cape Ann Whale Watch. This remarkable excursion, led by expert guides, introduces newcomers to the fascinating world of whales and their natural habitats. Finally, culinary aficionados can enjoy fresh seafood at Seaport Grille while taking in a scenic outdoor setting overlooking the water

Rockport

Coastal charm meets artistic heritage in this Essex County village. Situated on the tip of the Cape Ann Peninsula, Rockport offers plenty of beach getaways, with the most popular being Front Beach. This is thanks to its convenient location, within walking distance of downtown, with a rocky shoreline and access to restaurants and shops. The Rockport Arts Association & Museum serves as the regional cultural hub. It displays an array of pieces, contributed by hundreds of local creatives, and promotes an artistic culture by hosting lectures, classes, and demonstrations for the public.

Rockport is also home to the unique Paper House, entirely made out of paper. The historic venue is the brainchild of Elis Stenham, who used more than 100,000 copies of newspapers to create furniture, a grandfather clock, and other home furnishings. Finally, those who want to take it easy can enjoy a laid-back game of golf at the Rockport Golf Club, taking in cool breezes and stunning ocean views.

Nantucket

Nantucket is a serene island destination off the coast of Cape Cod, beloved for its dune-filled beaches, picturesque lighthouses, and a string of historical landmarks. Tourists come to marvel at the 46-foot skeleton of a sperm whale at the Nantucket Whaling Museum. This unique museum, housed inside a mid-19th-century candle factory, boasts a mix of rotating and permanent exhibitions across multiple premium galleries, sharing fascinating folklore about the history of whaling in the area. The Great Point Lighthouse is one of the distinct lighthouses in the town. Initially constructed in 1784 and rebuilt in 1986, it serves as a lasting symbol of Nantucket's enduring maritime heritage, situated on the northern end of the island.

Beaches are a stunning feature in Nantucket, offering an escape for those visiting the island to let their shoulders down and forget their troubles. Many tourists love heading to Madaket Beach, where a wide, sandy, and windswept beach allows guests to retreat and bask in spectacular sunsets while gazing out into the horizon.

Concord

Concord is a historically rich town northwest of Boston, often associated with the advent of the American Revolutionary War. It hosted the Battle of Concord, which marked the start of the war, and maintains critical monuments such as a replica of the North Bridge, where the first shots of the iconic war were fired. The Concord Museum paints a clearer picture of the town's cultural and political history. Touring the facility introduces visitors to over a dozen galleries with a diverse collection of artifacts, including pieces from the American literary renaissance and the influential Thoreau family.

Beyond the war history, Concord offers great outdoor pursuits at the Great Meadows National Wildlife Refuge. This 3,600-acre refuge serves as a habitat for hundreds of local and migratory bird species, including waterfowl, Canada geese, and song sparrows. It is the perfect escape for birders and wildlife enthusiasts, offering a break from the bustling downtown crowds.

Salem

This lovely coastal community gained nationwide notoriety during the Witchcraft Trials of 1692, an event immortalized in books, on screen, and in movies. Salem is among the most unforgettable small towns to visit in Massachusetts, offering a unique glimpse into the trials at the Witch House. This 17th-century dwelling belonged to Judge Jonathan Corwin, who directly presided over some of the trial cases and is the only structure in town with direct links to the infamous event. The Salem Pioneer Village is America's maiden living history museum. It depicts the community in 1630 and features 3 acres of wigwams, dugouts, and cottages.

The outdoors beckon nature lovers to hang out at Salem Willows Park. This 25-acre waterfront park boasts breathtaking views of the Salem harbor, offering a boardwalk, a sandy beach, an arcade, and picnic benches under shady trees.

Northampton

Northampton is a vibrant college town in Hampshire County, serving as a melting pot for the arts, history, and nature. The community lures art aficionados with numerous opportunities, including admiring diverse pieces at R. Michelson Galleries. Western Massachusetts' largest commercial gallery features a collection of watercolors, oil paintings, fine art books, and prints. Alternatively, you can enjoy passionate live music performances at the Academy of Music. This storied 19th-century theater has a 1,000-seat capacity and showcases a lineup of productions by local and touring acts, including the Northampton Players.

Elsewhere, the Botanic Garden of Smith College offers a nice spot to relax and reconnect with nature. It consists of a diverse collection of tropical and subtropical plants, including thousands of woody trees, hardy herbs, and woody plants, with quiet walking paths winding through the peaceful oasis.

Lenox

Lenox is a gem in the Berkshires of western Massachusetts, opening doors to serene natural spaces, world-class arts, and stunning Victorian mansions. The town is notably home to Tanglewood, where the Boston Symphony Orchestra has performed since 1937. This world-renowned venue hosts a seasonal series of concerts, featuring a diverse range of artists from pop, classical, and contemporary genres. Edith Wharton's Home is one of the unmissable historical estates in Lenox, offering a glimpse into the past. Built at the start of the 20th century, the property features a grand mansion surrounded by lush and beautifully landscaped gardens, where people can enjoy quiet picnics and participate in fun cultural events.

Lenox entices outdoor lovers with secluded escapes at Pleasant Valley Wildlife Sanctuary. Set amidst over 1,000 acres of greenery in the foothills of the Berkshires, this vast natural space offers winding trails through wetlands and meadows, rewarding hikers with views of local wildlife, particularly hardworking beavers.

Great Barrington

Great Barrington is the ultimate haven for outdoor adventurers, promising exciting recreational opportunities throughout the year. The town of Ski Butternut is a popular winter sports destination, boasting world-class slopes that feature at least 100 acres of skiable terrain, 22 skiing trails, and 10 chairlifts. Hikers can have a blast discovering the isolated and rugged trails that traverse the densely wooded Monument Mountain Reservation. Spanning over 500 acres, the park offers a wide range of recreational activities, including picnicking, birding, hunting, hiking, and skiing. Seasoned hikers can ascend to the 1,600-foot summit of Peeskawso Peak for breathtaking views of the surrounding landscapes.

Beyond the outdoors, Great Barrington engages art lovers with moving performances at the Mahaiwe Performing Arts Center. This early 1900s venue hosts operas, concerts, dramas, movies, theater, and other live productions throughout the year.

Final Thought

From the Witchcraft Trial in Salem to the Revolutionary War battle sites in Concord, these unforgettable small towns to visit in Massachusetts bring out the best of the state’s rich heritage and scenic charm. Together they weave history, culture, and New England spirit into every mountain trail, cobblestone street, and coastal vista. Whether you’re drawn to seaside sunsets, colonial landmarks, or artsy hamlets tucked into rolling hills, each offers a unique and memorable slice of charm.