Massachusetts has of trail. The entire section of trail is in western Massachusetts' Berkshire County. It summits the highest peak in the southern Taconic Range, Mount Everett (), then descends to the Housatonic River valley and skirts the town of Great Barrington. The trail passes through the towns of Dalton and Cheshire, and summits the highest point in the state at , Mount Greylock. It then quickly descends to the valley 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.