History and community in the Berkshires
Great Barrington is a community known for its surrounding landscape, set in the Berkshire Mountains of western Massachusetts with the Housatonic River winding through its center. Here, historic homes and quiet neighborhoods blend with a steady flow of visitors—some arriving to hike Monument Mountain or catch a show at the Mahaiwe Performing Arts Center, others drawn by the changing leaves or the ski slopes in winter. “Often, people move here after enrolling their children in nearby boarding schools, and before they know it, they’ve decided to stay for good,” says Mary Naylor, a longtime resident and local real estate agent. “There’s a serenity here that draws people in.” Streets reflect both the rhythms of daily life and the energy that comes with being a vacation destination. This particular Berkshires pocket is considered the pricier housing market, making it less accessible for first-time buyers. Still, countless visitors fall in love with the area and find ways to make it work. Naylor adds, “I spent 34 years as a flight attendant, traveling the world, but when I was ready for a quieter life, I found myself drawn back here." History is everywhere in Great Barrington, especially as the birthplace of civil rights leader W.E.B. Du Bois. The town proudly honors him with a historic homesite, walking tours and local landmarks that celebrate his lasting impact.
Historic 19th century homes
Many turn-of-the-century homes here have been passed down through families for generations. Classic farmhouses and Colonial homes date back to the 1800s, many of which have been renovated over the years. Victorian homes here have intricate woodwork and front-porches, and it’s not uncommon to find original details like wide-plank floors and hand-carved moldings. New construction is relatively rare, though there are still lots available open for those looking to build, often offering several acres of land and plenty of privacy. Depending on location and updates, larger five-bedroom properties often start around $700,000 and can exceed $2 million for estates with acreage or luxury finishes.
Career readiness at Monument Mountain High
Local kids can start school at Muddy Brook Elementary, which earns a B-plus from Niche, then continue to the B-minus rated W.E.B Du Bois Regional Middle School. Monument Mountain Regional High earns an A-minus, offering Innovation Pathways programs focused on Business and Finance, Health Care and Manufacturing.
Skiing Butternut and swimming in Mansfield
Ski Butternut has been a winter staple in Great Barrington since the 1960s, with a range of slopes for skiers of all abilities and a dedicated area for snow tubing that draws families during the colder months. When the snow melts, Lake Mansfield becomes a favorite gathering place, offering a swimming beach, picnic spots and a loop trail that winds through the trees along the water’s edge. Monument Mountain is a well-loved destination for hiking, with trails that climb through the forest to sweeping views of the Housatonic River Valley. Not far from town, Bash Bish Falls is a popular spot for day trips, where visitors hike through the woods to see the tallest waterfall in Massachusetts.
Shopping on Railroad and Main Street
Great Barrington’s walkable downtown centers around Railroad Street and Main Street, two historic thoroughfares lined with locally owned shops and eateries. Mornings often begin at Patisserie Lenox, where buttery croissants and raspberry macarons draw crowds to its sunlit café, while evenings shift to Bizalion’s Fine Food, a European-inspired market and bistro. For a sweet treat, Robin’s Candy here is a decades-old local institution.
The Berkshire Food Co-Op anchors the community with organic produce, bulk goods and a commitment to regional farmers. Cultural hubs like the Mahaiwe Performing Arts Center, a 1905 theater with 650 seats, host everything from indie film festivals to live jazz, while the Triplex Cinema screens arthouse films and cult classics. Between meals and shows, visitors browse Railroad Street Collective’s artist-made ceramics and apparel or explore Main Street’s boutiques, from Barrington Outfitters’ hiking gear to SETT’s handcrafted tableware.
Signature Berkshire arts events
Great Barrington’s calendar features two standout events that bring the community together each year. The Berkshire Bach Society’s New Year’s concerts are a longstanding tradition, drawing music lovers to the Mahaiwe Performing Arts Center for lively performances of Bach’s works by renowned musicians. Each June, the Berkshire International Film Festival takes over the Triplex Cinema, showcasing independent films, documentaries and shorts from around the world.
Tri-Town Connector and local transit
Residents have easy access to U.S. Route 7 and the Massachusetts Turnpike (Interstate 9 for trips throughout western Massachusetts. The Berkshire Regional Transit Authority (BRTA) operates several bus routes-including Route 21 and the 921 Express-that link Great Barrington with nearby towns like Lee, Lenox and Pittsfield, with stops at key locations. Fairview Hospital serves the community, and the Albany International Airport is about 56 miles away.
Four distinct seasons in the Berkshires
Great Barrington experiences warm, humid summers and cold, snowy winters. Rain and snow are spread pretty evenly throughout the year, which helps keep the area’s forests and rivers vibrant and healthy. The town faces stormwater runoff, erosion, and invasive plant species which can affect water quality and the stability of riverbanks. To help address these issues, local conservation efforts focus on protecting stretches of riverside forest and maintaining wildlife corridors.
