2025's Most Underrated Towns In Massachusetts

Massachusetts is steeped in American history, coastal charm, and New England character, yet many of its most captivating towns are quietly tucked away, often overshadowed by larger cities like Boston or popular vacation spots like Cape Cod. These small towns are rich with personality, offering scenic landscapes, unique attractions, tight-knit communities, and cultural depth. This list highlights eight of the most underrated towns in Massachusetts in 2025—perfect for travelers and prospective residents seeking authenticity without the crowds.

Rockport

Rockport, located on the tip of Cape Ann, is often bypassed by visitors heading for nearby Gloucester or the outer Cape. Yet this seaside town offers an extraordinary blend of natural beauty, cultural depth, and small-town tranquility. The town’s signature red fishing shack, Motif No. 1, is said to be one of the most painted buildings in the United States and is the focus of an annual community festival held in mid-May. Art galleries line Bearskin Neck, and the Shalin Liu Performance Center offers concerts with panoramic ocean views. Sandy beaches, coastal hikes at Halibut Point State Park, and lobster shacks round out the charm of one of the North Shore’s most rewarding destinations.

Great Barrington

Nestled in the Berkshires, Great Barrington is often eclipsed by neighboring towns like Stockbridge and Lenox. However, it possesses a dynamic blend of artistic flair, natural beauty, and community spirit. Downtown is filled with independent bookstores, local cafes, art galleries, and boutique shops. The Mahaiwe Performing Arts Center offers a year-round schedule of film, music, and theater. Outdoor enthusiasts can ski at Butternut Basin in winter or hike Monument Mountain in the warmer months. Its status as a vibrant yet low-key cultural hub makes it a gem for travelers seeking something a little more offbeat.

Shelburne Falls

This enchanting village in western Massachusetts is best known for its Flower Bridge—a decommissioned trolley bridge now overflowing with colorful blooms. Despite this beauty, it can be overlooked by tourists who are more focused on Pioneer Valley or the Berkshires. Shelburne Falls boasts a thriving arts scene, with artisan galleries, glassblowing studios, and a series of mosaic murals along the Riverwalk. The glacial potholes along the Deerfield River are a natural wonder, particularly stunning in spring and fall. The community is warm and welcoming, frequently hosting events such as the Heath Fair agricultural festival, held annually in August.

Ipswich

Despite being one of the oldest towns in America and boasting a hard-to-match collection of 17th-century homes, Ipswich tends to receive less notice than the nearby towns of Salem and Newburyport. Located along the North Shore, Ipswich is rich in colonial and maritime history. It is home to the Crane Estate, a grand early 20th-century mansion overlooking miles of conservation land and beach, all of which are now open to the public. The Ipswich River offers kayaking and peaceful walks, while the aforementioned Crane Beach is one of the most pristine stretches of sand in the state. The town also has a growing food and beer scene, another factor that makes Ipswich’s relative lack of crowds a pleasant surprise.

Deerfield

Historic Deerfield is a beautifully preserved colonial village that provides a living history experience unlike anywhere else in New England. Despite this, it is not a tourist-heavy destination on the level of Concord or Plymouth. The town features restored 18th- and 19th-century homes and museums showcasing early American life, all nestled among maple trees and stone walls. The Pocumtuck Valley Memorial Association curates one of the best regional history museums in the area. Beyond history, the surrounding Pioneer Valley offers four seasons of outdoor adventure in the form of hiking, river rafting, mountain biking, cross country skiing, and more.

Orleans

Although it sits on Cape Cod, Orleans often gets passed over for flashier destinations like Chatham or Provincetown. That makes it an ideal place for those seeking natural beauty and serenity without the tourist crush. Orleans is bordered by both the Atlantic Ocean and Cape Cod Bay, offering easy access to Nauset Beach and Skaket Beach. The town’s compact downtown is home to bookstores, art galleries, and locally owned restaurants, and hosts annual events like Arts Week in April and the Cherry Blossom Festival in May. Orleans also offers access to the Cape Cod Rail Trail, which winds for 25 miles through forests and salt marshes.

North Adams

Situated in the northern Berkshires, North Adams has a rugged post-industrial beauty and a thriving arts scene, anchored by MASS MoCA—one of the largest contemporary art museums in the U.S. North Adams has also revitalized its downtown, which hosts an annual community celebration in August, with cafes, galleries, and creative workspaces. The surrounding hills offer hiking and skiing, especially on Mount Greylock, the highest point in Massachusetts. The town’s transition from mill town to creative outpost is impressive, yet its gritty aesthetic and industrial past mean it is still a hidden gem for those outside the immediate area, who are not aware of its transformation.

Hingham

Located south of Boston on the South Shore, Hingham is a coastal gem that often gets bypassed for the more well-known Cape Cod towns. However, the town’s quiet charm and refined character offer visitors a perfect blend of history and nature. With a walkable harbor, historic Main Street, and colonial architecture, Hingham feels like a movie set. It is home to the Derby Academy (founded in 1784), and several of the oldest churches and homes in the state. The town also boasts World’s End, a stunning Trustees of Reservations park with coastal trails and sweeping waterfront views.

Massachusetts is full of well-known destinations, but its lesser-known towns are often the places where the real magic happens. These eight underrated gems offer a deeper, quieter, and more meaningful experience of the Bay State. Whether you are looking for nature, history, art, or local flavor, each of these towns offers something unique without the crowds. As 2025 unfolds, consider stepping off the main road to discover what these remarkable small towns have to offer. You may just find your new favorite place!