Living in Great Barrington, MA

About Great Barrington

The Mahican name for this stretch of the river was Mahaiwe, "the place downstream." Colonists settled here in 1726, the area served as the north parish of Sheffield from 1742, and it was incorporated as Great Barrington in 1761. In 1774 local colonists forced the Berkshire County court to close in protest of British policy, and in March 1886 William Stanley's alternating current system lit 23 businesses along Main Street. That Main Street still carries US 7 through the central village, where the Mahaiwe Theater opened in 1905 and reopened in 2005 as a performing arts center.

North of the center, the village of Housatonic grew in the early 1800s around textile and paper mills on the river; Monument Mills, which had 500 employees at its peak, closed in 1956, and the mill buildings are listed on the National Register. Monument Mountain rises along Route 7, with 503 acres and a 1,642-foot summit kept by The Trustees. To the east, East Mountain holds Ski Butternut and a state forest crossed by the Appalachian Trail. The Housatonic River Walk follows the river through downtown, and the W. E. B. Du Bois Boyhood Homesite, a National Historic Landmark, lies on the road to South Egremont.

Great Barrington's housing ranges from the Taconic and West Avenues Historic District south of downtown, where about two-thirds of the buildings date from 1890 to 1910, to recent nonprofit rentals. The Community Development Corporation of South Berkshire had Bentley Apartments, 45 affordable units on a former log-home factory site at 100 Bridge Street, under construction by February 2020, and with Way Finders opened Windrush Commons, 49 rental units in five buildings at 910 South Main Street, in June 2023. In December 2025 the state found the town eligible for its Seasonal Communities designation; the town planner told Town Meeting that seasonal units make up 12.71 percent of the housing stock. Voters accepted the designation in May 2026, giving the town up to 24 months to adopt any required zoning changes, and in an advisory vote declined, 94 to 31, to urge a residential tax exemption.

Homes in Great Barrington

Seasonal use shapes Great Barrington's housing. In December 2025 the Commonwealth identified the town as eligible for its Seasonal Communities designation, whose criteria include the share of housing units used for seasonal, recreational or occasional use. Voters at the Annual Town Meeting that opened on May 2, 2026 accepted the designation, which does not change local regulations by itself, and the Selectboard and Planning Board scheduled a joint meeting on related zoning changes for June 1, 2026.