Great Barrington is located in the picturesque Berkshire Hills in western Massachusetts. The Berkshires are widely known as the premier summer cultural destination of the Northeast. Tanglewood, home of the Boston Symphony Orchestra; Shakespeare and Company, Jacob's Pillow Dance Festival, Berkshire Theatre Festival, the Norman Rockwell Museum, the Clark Art Institute (just to name a few) are nearby.

The Berkshires also boast some of the East coast's best paddling, biking, fishing and hiking opportunities. The Appalachian Trail cuts a swath through the county; the Housatonic River and hundreds of lakes are nearby; and bikers enjoy hundreds of miles of both mountainous terrain and leisurely "flats" to pedal in.

Great Barrington is about an hour southeast of Albany, and New York City and Boston are within three hours by train or bus. In short, the Berkshires are "the place to be" during the summer months - as the traffic tends to flow West from Boston and North from New York between June and September. The closest major airports are Albany and Hartford Springfield (Bradley International). East Coast train and bus services also are available to within an hour from Great Barrington.