 From Berry Pond, the trail descends the ridgeline into the village of Hancock, Massachusetts, then ascends the second ridge, which straddles the New York border.Features along this section include Rounds Mountain, Misery Mountain, Berlin Mountain (the trail's high point), Mount Raimer, White Rock, and a crevasse called the Snow Hole where ice has been known to persist year round.The trail utilizes conservation land and easements including the Taconic Ridge State Forest (NYSDEC) and Hopkins Memorial Forest, owned and managed by Williams College.