The Cross-West Tisbury trail begins at Blackwater Pond Reservation, a beautiful place to see birds and enjoy pond views. It leads up through the woods and swamps of Wompesket and then down through fields at the John Presbury Norton Farm. Near the intersection of the Old County and State Roads, it follows the Old Holmes Hole Path, a Special Way through the woods and behind houses, leading towards the West Tisbury School.

At the intersection of the Dr Fisher Road, the path goes southeast through the State Forest leading to the bike path, parallel to the West Tisbury-Edgartown Road. Go west on the bike path and then cross the road and take Deep Bottom Road as it leads southwest towards Tisbury Great Pond. Take a right on Bradley Martin Road as it goes west to Tiah’s Cove Road. Finally, take a left on Clam Point Road and enter Sepiessa Point Reservation. The trail, along coves and through the woods ends at a point with beautiful views of Tisbury Great Pond and the ocean beyond.