 The entire section of trail is in western Massachusetts' Berkshire County; it traverses both the Taconic Mountains and the Berkshires.The A.T. climbs the highest peak in the southern Taconic Mountains, Mount Everett (), then descends to the Housatonic River Valley and skirts the town of Great Barrington.From there, it ascends into the Berkshires and passes through the towns of Dalton and Cheshire.