6 Standout Main Streets In Massachusetts

Where else can a single Main Street show three centuries of American life within one short walk? Massachusetts is divided into diverse regions: the fishing ports along the Atlantic coast, the industrial belt through the center, and the farmland in the west. Founded in the 1600s, Massachusetts developed through self-governed towns connected by early turnpike roads and the Boston Post Road. Most of these towns have a Main Street where public buildings and local businesses remain in daily use, offering a glimpse into early planning principles and how they continue to define New England towns. Prepare your walking shoes and explore any of these downtowns.

Concord

Fun fact: Main Street in Concord still follows the path of the original colonial road, laid out before the American Revolution. It's a good idea to start the day at Barrow Bookstore, located in a restored carriage house that specializes in Concord history and works by local authors such as Ralph Waldo Emerson and Nathaniel Hawthorne. It was named one of the top independent bookstores in the United States by USA Today readers in 2025. Nearby, Three Stones Gallery displays regional paintings, sculpture, and photography in a compact, light-filled space.

Less than a mile from Main Street, visitors can tour the Orchard House, where Louisa May Alcott wrote Little Women, and see how her family lived and worked during that time. The Ralph Waldo Emerson House opens in April, offering a glimpse into the preserved interior of Emerson’s home and highlighting Concord’s literary history. Visitors can end their day at the South Bridge Boathouse, renting canoes and kayaks to paddle the shaded stretch of the Sudbury River.

Northampton

Since 2019, Northampton’s main street has undergone a city-led redesign with improvements that increased accessibility for walking and cycling while supporting local businesses recovering from the COVID-19 pandemic. Many people start their journey at the Historic Northampton Museum, which houses a 19th-century barn with exhibits displaying farming equipment, Civil War letters, and early photographs.

A short three-block walk east is R. Michelson Galleries, which displays contemporary sculptures and original children’s book illustrations in a former bank building. Directly across the street, PINCH sells locally made ceramics, textiles, and handmade jewelry in a quiet storefront. A typical day ends with a visit to the Academy of Music, a 100+ year-old performance venue that remains active today. On November 12, 2025, the Academy will host Olmsted Panoramic, an evening program on public parks with an electric cello, all within a ten-minute walk from start to finish.

Falmouth

Katharine Lee Bates, the writer of America the Beautiful, was born on Main Street. Visitors can see the historic clapboard home at 16 Main Street, which is identified for those interested in local history. After that, visitors often continue to the Museums on the Green, part of the Falmouth Historical Society, housed in two 18th-century buildings with exhibits on maritime history, early settlement, and the Underground Railroad. Nearby, Eight Cousins Books, an independent bookstore known for Cape and Island authors, offers a wide selection and regularly hosts New England writers for literary events.

Across the crosswalk, Main Street Gallery Fine Art showcases regional artwork, including coastal photography and sculpture by Cape artists, inside a historic storefront. For a breath of fresh air, Peg Noonan Park offers a small green with benches and a performance area used in summer for outdoor concerts and art festivals. Each December, Main Street becomes the center of Falmouth’s Holidays by the Sea Weekend, when shops stay open late for carolers, vendors, and the annual parade.

Great Barrington

The walkable section of Main Street passes by Great Barrington’s public library, parks, and converted bank buildings now used for food shops and art venues. Many visitors begin at the Mason Public Library, a 1910s stone building that hosts Teen Time programs and weekly activities like LEGO at the Library. It is a short walk to Stanley Park, a small grassy area surrounded by large trees, with a play area often used by local families.

Then, a must-stop in Great Barrington is Rubiner’s Cheesemongers. It occupies a former bank building on Main Street, where the old vault holds imported cheese and gourmet foods. Most visitors end their day at the Mahaiwe Performing Arts Center, a 1905 theater with lush seating and original architectural details that hosts films, lectures, and live music.

Stockbridge

Long before Stockbridge became known for its Christmas streetscape, a small café on Main Street inspired Arlo Guthrie’s Alice’s Restaurant. Even though the original restaurant has been closed for many years, the location remains a reference point for people who know the song and its Thanksgiving tradition. The next-door Red Lion Inn anchors the community with wooden floors, afternoon tea, and a porch that has looked out on Main Street since 1773.

Across the street, Image Photo Gallery features local photographers who capture Berkshire landscapes and portraits in a bright storefront. Directly behind Main Street, the Norman Rockwell Museum houses the artist’s studio and hundreds of Rockwell’s originals, including Stockbridge Main Street at Christmas (1967). Each year, the town recreates that scene during Stockbridge Main Street at Christmas, when vintage automobiles, wreaths, and carolers transform the street into Rockwell’s painting for two days.

Lee

Many may know that marble from Lee built part of the U.S. Capitol and still gleams in the statues of Philadelphia’s City Hall and New York’s St. Patrick’s Cathedral. The day begins at the Starving Artist Creperie & Café, which serves breakfast made with local ingredients and rotates art exhibitions, doubling as a small gallery space. A short distance down the road, the Lee Public Library occupies a 1907 Romanesque Revival building with broad marble steps that reflect the town’s quarrying history. Across the street, the Spectrum Playhouse operates in a converted church, presenting community theater, live music, and film screenings.

At the far end of Main Street, the restored 1800s storefronts house the Main Street Market, offering regional produce, cheese, and handmade crafts. Laurel Lake provides a quiet place to rest and watch the light on October Mountain. Every September, Main Street fills with parades, concerts, and antique cars during Lee Founders Weekend, celebrating the town’s 1777 charter.

A Living Record Of Massachusetts

Main Street in Massachusetts is more than a road; it reflects how each town preserves its history and how people continue to use it. Northampton and Great Barrington show how small towns can recover from change while keeping their centers active. Concord and Falmouth preserve literary and maritime heritage within their daily routines. Lee and Stockbridge maintain 19th-century patterns of inns, galleries, and gathering places still in use today. Together, they show a state that keeps its history working as part of everyday community life rather than setting it aside as a display.