Great Barrington

Great Barrington is a town of 7,172 people in the Housatonic River valley of southern Berkshire County, Massachusetts, including the villages of Housatonic and Van Deusenville. It was a Gilded Age resort town where wealthy New Yorkers built Berkshire cottages in the hills, and in 2012 Smithsonian magazine named it the best small town in America. It is also an official Appalachian Trail Community. The modern town mixes that inheritance — grand houses, a 1905 vaudeville theatre, estate roads — with a working Main Street of restaurants, bookshops and farm stores, and it serves as the southern Berkshires' year-round hub.

The Mahaiwe Performing Arts Center anchors the culture, with concerts, dance, theatre and film on Castle Street through the year. The W.E.B. Du Bois Boyhood Homesite honours the scholar and civil rights leader born in Great Barrington in 1868, and Searles Castle recalls the cottage era at full scale. In 1886 William Stanley demonstrated the first practical alternating-current lighting system on Main Street, lighting 23 businesses — electrical history made in a small town. Outdoors, trails climb Monument Mountain for views over the valley, the Appalachian Trail crosses the town's southeast corner, and Ski Butternut stands on East Mountain at the edge of town. The Guthrie Center, in the old Trinity Church of 'Alice's Restaurant' fame, hosts concerts and community meals in Van Deusenville. At the western edge of town stands the Newsboy statue, presented to Great Barrington in 1895 and still one of its landmarks.

Railroad Street is the dining row: a block of restaurants, cafés and bars just off Main Street, joined by farm-to-table rooms, bakeries and the Great Barrington Farmers Market, which fills Church Street on Saturday mornings from May into the fall. BerkShares, the region's local currency, circulate in the town's shops. The Triplex Cinema and the Mahaiwe cover film, and the Berkshire International Film Festival takes over the town each June. Evenings end early by city standards, but in summer the patios stay full and Berkshire Busk! fills the downtown sidewalks with street performers on Friday and Saturday nights.

Stay in the inns and boutique hotels on and around Main Street, in bed and breakfasts on the estate roads, or in motels along Route 7; campers use Beartown State Forest and private grounds in the hills. The centre is compact and walkable, Berkshire Regional Transit Authority buses link the Berkshire towns, and Peter Pan and Greyhound coaches stop on Main Street for New York and Boston. The nearest Amtrak station is Pittsfield, about 20 miles north.

Summer is peak — theatre, music, the film festival and the hills at their greenest — and October brings the foliage crowds. Winter belongs to Ski Butternut, busiest from December to March, and spring is the quiet season of waterfalls and empty trails. Two or three nights make a proper base for the southern Berkshires; the town rewards a slower stay more than a pass-through.

Great Barrington sits on U.S. Route 7, the Berkshires' north–south spine: Stockbridge, Lenox and Pittsfield are to the north, Sheffield and Connecticut to the south, and Route 23 runs east–west through town. The Massachusetts Turnpike (Interstate 90) passes just north at Lee. Albany and Hartford are each about an hour away and New York under three hours, making Great Barrington the natural overnight stop between the Hudson Valley, the Berkshires and the Pioneer Valley.