Great Barrington is, in essence, the Brooklyn of the Berkshires. The town flourishes from an expansive quantity of unique shops, restaurants, and B&Bs—among many other lively activities—playing into an almost urban ambiance. For many, this is a 2nd home town and four-season tourist community. Both Main Street and Railroad Street have delicious eateries and cafes, as well as a good assortment of shopping and entertainment. Also, check out the weekly farmer's markets in the warmer seasons. Beyond the upscale urbanesque areas, many scenic hiking locations can be found throughout the town as well, including Monument Mountain State Reservation. Then, as winter approaches, Great Barrington can transition into a bit of a ski town, as this is where Ski Butternut is located (and Catamount is nearby).

There is a great blend of culture and character here. The Smithsonian magazine has even ranked Great Barrington as the best small town in America. W.E.B Du Bois, a significant civil rights activist (among many other feats), was born in this southern Berkshire County town, too. Great Barrington functions as a popular summer resort for many people who love the surrounding nature and wonderfully eccentric venues. When traveling throughout the streets, visitors are treated to views of Berkshire Cottages—grand houses built by wealthy families during the development of the area. Exploring Great Barrington is a true pleasure for all of the senses. Situated halfway between Albany and Hartford in the southwestern corner of the commonwealth, it's the most accessible Berkshire town from New York City—best accessed through the scenic rural towns of northeast Connecticut. There is something for everyone in Great Barrington.