Massachusetts has of trail. 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. It ascends into the Taconic Mountains again, visiting Mount Greylock, the highest point in the state at . It then quickly descends to the valley of the Hoosic River within of North Adams and Williamstown, before ascending again to the Vermont state line. The trail throughout Massachusetts is maintained by the Berkshire Chapter of the Appalachian Mountain Club.