7 Small Towns in Massachusetts with the Best Downtowns

Newburyport rebuilt Market Square in brick after the 1811 fire. The brick is still there. Concord’s Monument Square still anchors the streets where the Revolution started. Provincetown’s Commercial Street has been an art colony longer than any other in the country. Massachusetts small towns kept their downtowns when most of the country lost theirs. Seven of those downtowns below.

Oak Bluffs

This small town is located on Martha’s Vineyard, and its downtown district is known for the brightly painted Gingerbread Cottages and access to the beach. The cottages date back to the 19th century and feature Victorian architecture with colorful hues and gingerbread trims. Downtown Oak Bluffs is centered on Circuit Avenue and offers a walkable district of locally owned businesses. The town fills with tourists arriving on the ferry in summer, giving Oak Bluffs a mix of New England small-town character and the energy of a popular beach town. Just off Circuit Avenue, visitors can grab a drink at Giordano’s Restaurant, Inc., a long-running Italian spot serving pizza and family meals. Opposite the restaurant is the 19th-century Flying Horses Carousel, the oldest operating platform carousel in the United States.

Northampton

Northampton is a college town with an arts-heavy downtown. The downtown district is walkable and full of independent businesses and a strong food scene. As home to Smith College, Northampton has a collegiate atmosphere. Thornes Marketplace is a multi-story indoor arcade with over 25 local shops and restaurants. The historic building is a central destination downtown. Main Street anchors the district and now features restored 19th-century architecture housing shops, cafes, and galleries.

Main Street is particularly known for its bookstores. The Academy of Music Theatre is an 1891 venue that hosts live performances, films, and community events. The Calvin Coolidge Presidential Library and Museum, located at the Forbes Library, is dedicated to the 30th U.S. president, who was once mayor of Northampton. In addition to its collection of American and European art of the 19th and 20th centuries, the Smith College Museum of Art also features quirky artist-designed restrooms for visitors to explore.

Newburyport

This maritime town is known for its preserved brick downtown, which sits on the waterfront, offering seaside dining and locally owned boutiques. The Downtown Newburyport district sits at the mouth of the Merrimack River and is known for its Federalist-era brick architecture and cobblestone streets. During its history as an important maritime hub, the Great Fire of 1811 forced a rebuild with brick structures.

The center of downtown is Market Square, at the intersection of State, Water, and Merrimac Streets. The square features dense rows of brick commercial buildings. Inn Street is a pedestrian walkway lined with small boutiques and known for its floral displays. The Tannery Marketplace is a historic mill that has been preserved and repurposed as a commercial complex featuring shops, restaurants, and galleries. Visitors can spend time shopping at spots like the Jabberwocky Bookshop or enjoy a pizza at EPICUREO Pizza. Every summer, in July or August, the Yankee Homecoming takes place. This summer festival features parades, music, and waterfront events.

Stockbridge

This small town in the Berkshires is a classic of its kind, a rural town noted for its fall color and close-knit community. The Red Lion Inn, built in 1773, is known for the rocking chairs on its front porch. The historic downtown district holds shops, galleries, and cafes that capture the everyday character of New England towns.

Located a short drive from downtown, the Norman Rockwell Museum celebrates the life and work of the artist, including his preserved studio. Also close to downtown is Naumkeag, a large late-19th-century Gilded Age cottage with well-maintained gardens. Back on Main Street, The Mission House, built around 1740, depicts the lives of New England colonists and their relationship with the Mohican people.

Norman Rockwell lived in Stockbridge, and his painting Stockbridge Main Street at Christmas is a celebrated piece of Americana. The Christmas season is celebrated over a weekend in December, with Stockbridge Main Street at Christmas, centered on Rockwell’s painting. The event features historic property tours, a Winterlights display, and holiday markets.

Provincetown

This town features an active, artistic downtown district centered on Commercial Street. Located on Cape Cod, Provincetown’s downtown is a walkable and historical seaside district. The town is celebrated as a welcoming center for the LGBTQ+ community and as the United States’ oldest continuous art colony. The town and its downtown district feature a large number of galleries, as well as independent shops and restaurants, right next to the area beaches and the MacMillan Pier. Some of the most popular include the Four Eleven Gallery and Gallery 444 Ptown, both located on Commercial Street.

The Provincetown Art Association & Museum is a key artistic hub for galleries and the town’s status as a historic art colony. Two other town districts, the East End and the West End, are quieter, with shops and galleries in the former, and residential streets with historic homes in the latter. After learning about the town’s artistic history, head to the beach to take a tour of the Dune Shacks of Peaked Hill Bars Historic District. The district features nearly 2,000 acres of protected sand dunes and the dune shacks that were once the homes and studios of artists and writers. For those visiting, the town is accessible by ferry from Boston and gets crowded during the summer tourist season.

Great Barrington

Located in the Berkshires, Great Barrington has a working downtown district centered on Main Street. The Cultural District, part of downtown, is the commercial and cultural hub for Southern Berkshire County. Many sites anchor downtown, such as the 1905 Mahaiwe Performing Arts Center, which features year-round live performances, movies, and events.

History runs through the town. Main Street was one of the first U.S. streets to have electric lights, and was the childhood home of writer and Black activist W.E.B. Du Bois. The nearby W.E.B. Du Bois Boyhood Homesite marks the location of his early life and sits within a larger protected landscape just outside downtown. The River Walk runs directly behind Main Street’s shops along the Housatonic River, offering a quieter stretch with views of the water and easy access points from the downtown. In May, ArtWeek Berkshires brings open studios, gallery events, and performances across the town, while Berkshire Busk! fills downtown Great Barrington with musicians and street performers during select summer weekends.

Concord

Concord is a small town steeped in American history, with many colonial and Revolutionary War sites. Downtown Concord, or Concord Center, is a historic cultural district centered around Monument Square, where several of the town’s oldest civic buildings still stand. The main commercial stretch along Main Street, known as The Milldam, reflects Concord’s independent spirit through its mix of local shops, galleries, and cafes housed in preserved historic buildings.

In town, the Concord Free Public Library holds extensive collections tied to the area’s literary past. Author’s Ridge, located in Sleepy Hollow Cemetery, is the final resting place of Ralph Waldo Emerson, Nathaniel Hawthorne, Louisa May Alcott, and Thoreau. Nearby, Orchard House remains one of the most recognizable landmarks, where Alcott wrote and set Little Women in the 1860s.

Great Downtown Districts of Small Town Massachusetts

Massachusetts holds onto its small-town downtowns as commercial, cultural, and community centers. Whether coastal towns with a maritime history or rural getaways in the Berkshires, the seven above each work the same formula differently. Old buildings still in use, shops and galleries doing real business, and streets that move at human pace.