The 4.1 mile Cross-Tisbury trail begins with a nice view of the Lagoon at the Ramble Trail/Brightwood Park property. It follows a trail through the woods and follows Winyah Lane briefly before it turns onto Winyah Circle and follows Bare Hill’s trail #2 up to the Vineyard Haven-Edgartown Road. After you cross the road, there is a lovely field trail uphill and into the woods at Bare Hill Preserve. After Sailor’s Burying Ground, you connect to the woods trails at Wapatequa leading you south towards Stoney Hill Road and Thimble Farm.

Trail #5 at Little Duarte’s, along the edge of the farm, leads you to the Greenlands Connector. A short walk along the northern trail at Greenlands then takes you to Four Corners (by the State Forest paved bike path) and the beginning of the Cross-Oak Bluffs trail.