Great Barrington: A Community in Motion

By Jamie Larson | David McIntyre | Winter 2025 | Community Spotlight

David McIntyre

Zip Code: 01230

Population: 7,172

Median Household Income: $82,484

Proximity to Major City: 108 miles from New York City; 137 miles from Boston

Transportation: The town is served by Route 7 through downtown and is approximately 12 miles south of Interstate 90 (Massachusetts Turnpike). Peter Pan and Bonanza regional buses serve the area, and the nearest Amtrak service is available in Hudson, New York, about 40 minutes away.

Nearest Hospital: Fairview Hospital, part of Berkshire Health Systems, is located within town at 29 Lewis Avenue.

Schools: The Berkshire Hills Regional School District includes Muddy Brook Regional Elementary School, W.E.B. Du Bois Regional Middle School, and Monument Mountain Regional High School. Private schools include Berkshire Waldorf School and more in the surrounding area.

Points of Interest: Mahaiwe Performing Arts Center, Ski Butternut, Monument Mountain, Norman Rockwell Museum, The Mount (Edith Wharton’s Home), Tanglewood, Jacob’s Pillow Dance Festival, Berkshire Botanical Garden, W.E.B. DuBois National Historic Site, Housatonic River Walk, Great Barrington Farmers’ Market, and the Triplex Cinema.

Great Barrington, Massachusetts, is a small town with a big paw print in the woods of the southern Berkshires, a place where cultured, well-heeled crowds from New York and New England mingle with local farmers, artists, and entrepreneurs. This mix of culture and community has made it super attractive to home buyers. However, while the town has been booming for a while, longtime residents have been feeling the pinch. More affluent visitors and residents, many of whom came during the pandemic, have found reason to lay down roots, while workers and families have found themselves priced out. Stakeholders are looking for balance, but solutions feel elusive.

“Maybe I’ve lived here too long, but I’m not sure Great Barrington really has [one] personality. It’s such a mix,” says Michelle Kaplan, a local writer, DJ, and cultural instigator. “What I do love, though, is when people don’t just complain about what’s missing. Instead they bring their own passion and make something happen. You shouldn’t be allowed to complain if you’re not actively organizing something.”

Snapshot: Great Barrington’s Strong Real Estate Market

The Great Barrington housing market remains strong and in demand. As of late 2025, the median listing price for a home hovers around $710,000, according to Realtor.com. Sale prices were up roughly 24 percent year-over-year by fall 2025, following a pandemic-era boom that saw many urban buyers relocate for more space, security, and scenery. Inventory is slowly rising across the county, but in Great Barrington, supply remains low and demand high.

According to the Berkshire County Board of Realtors, the number of homes sold in southern Berkshire County increased 10 percent in the first three quarters of 2025, even as average prices stabilized. The mid-market ($300,000 to $500,000) is the most active, but luxury homes continue to move fast.

Culture and Color

Great Barrington has long been an arts and culture destination. The Mahaiwe Performing Arts Center, Saint James Place, and the Great Barrington Public Theater serve as performance anchors. Each June, the Berkshire International Film Festival brings a touch of Hollywood to the Triplex Cinema. But there are also weirder, scrappier cultural happenings like the Berkshire Busk outdoor performance festival.

Greg Ward with his daughter Eva Ward and nephew Sam Ward in the greenhouse at Ward’s Nursery and Garden Center on Main Street.

Kaplan was behind the recent Sunshine Orange Subaru Crosstrek Parade, an absurdist event that confused and captivated the community with an inexplicable procession of orange Subarus in town in September.

Newer fixtures include Hy’s Fried, a chicken restaurant and dance club in Egremont that has become a destination for real, unpredictable experiences over the past year. A short drive away, Hilltown Hot Pies is slinging Neapolitan-style pizza with wild toppings, a Southern Italian wine list, and an emphasis on cross-table conversation. Both joints reflect a broader Berkshire trend: Locals creating spaces that are more than a business, they are community-forward, stylistically engaging, and deeply personal.

Downtown, the arrival of Eileen Fisher’s sustainable clothing lab this year signaled a different kind of investment. “We fell in love with the warmth of the community, the beauty of the space, and the like-minded approach to sustainability and slow fashion,” says store lead Liza Herrmann. Eileen Fisher doesn’t just sell clothes—it’s also the brand’s second ever “lab” concept, selling clothes that have been refurbished or made from sustainable and recycled materials.

Schools on Top of Mind

Refill GB offers home goods and bulk refills for hair and body care products.

Great Barrington is home to the Berkshire Hills Regional School District. A $152 million rebuild of the high school is underway, aimed at adding modern labs, sustainability features, and community-facing spaces. Until recently, the town was also home to Bard College at Simon’s Rock. The closure of the early college campus this year led to the loss of 200 jobs and left a sprawling 275-acre site dormant. Stakeholders have been working on a number of proposals for the reuse of the site. A nonprofit dubbed Simon’s Rock Village is raising funds to reimagine the space as a hub for housing, arts, and recreation. Local arts leaders, including Great Barrington Public Theater’s Jim Frangione, see potential. “It’s a loss, but it could also be an opportunity if we play our cards right,” he says.

Challenges and Outlook

Housing affordability remains a top concern in Great Barrington. With prices climbing, town government has enacted short-term rental regulations and continues to explore ways to encourage more affordable and workforce housing. A lack of infrastructure in surrounding hamlets like Housatonic remains a concern, but efforts are underway.

Despite the strain, Great Barrington remains a place of experimentation and reinvention. The community is defined less by a single identity than by its many voices in motion. “This town rewards participation,” Kaplan says.

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