The of trail in Connecticut lie almost entirely along the ridges to the west above the Housatonic River Valley. The trail climbs ridges above the town of Kent, and then works its way past the Housatonic River to Falls Village, where it regains the heights. After the town of Salisbury, the trail ascends into the Taconic Range, crossing, in order: Lions Head, Riga Ridge, and Bear Mountain, after which the Massachusetts line is achieved at Sage's Ravine.