Tisbury Meadow Preserve’s dozen roadside acres are grassy and hilly; notable is the white oak near the hilltop with its shapely crown. The pasture along the ridge and down its slopes is leased by the land bank to a farmer for raising livestock, primarily meat chickens. At the base of the hill is the Mai Fane House, a farmstead restored by caretakers at no expense to the land bank; its scale in the context of the fields is a reminder of Vineyard architectural standards prevalent until the most recent decades. Geologists will especially like the red trail in the woodlands, as it follows the crest of a long esker.

Start in Vineyard Haven and travel on the State Road in the direction of West Tisbury; turn left 0.4 miles after the Lake Tashmoo overlook. The trailhead and bicycle rack are located here.