Great Barrington's restaurant scene is better than you'd expect from a town of its size — partly because weekend visitors from Boston and New York demand good food, and partly because the town has attracted a cluster of independent restaurateurs who prefer the Berkshires to the city.
Main Street is the spine of the dining scene. Prices are moderate by Boston or New York standards, and most places are unpretentious. The town has a strong farmers' market culture (Saturday mornings in season on Railroad Street) that feeds into menus that change with what's available locally. In summer, the demand from Tanglewood visitors pushes prices up and wait times out — book ahead on weekends.