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The Cross-Chilmark trail is 6.2 miles long. It begins on the north shore at Great Rock Bight Preserve with beautiful views across to the Elizabeth Islands. It travels south and east along the Holman Path and then heads sharply west into Middle Line Woods. From there it goes further west to Peaked Hill Reservation, the highest point of the island at 311 feet above sea level, affording beautiful views of the south shore. The trail finishes to the southeast at Fulling Mill Brook Preserve with its woodland trails and streams.