For the bicyclist, the Chappaquiddick coastline is so immense that even a short stroll down the beach brings privacy. An incredible cross section of the Vineyard, encompassing bicycle trails, rolling farmland and ocean views, can be seen along this route. For the next 4 miles, enter a world free of cars and mopeds as you sweep by fragrant pine trees and scrub oak barrens. I recommend taking South Road or Middle Road on the way out and return on North Road. South and Middle Roads have more hills, but the ocean and farmland views are spectacular.
North Road is flatter, making for an easier return trip.
If you choose to start on South Road, be sure to stop off at the Field Gallery in West Tisbury Center. This outdoor gallery provides a playful display of large, white, humanistic statues, frozen in a favorite dance step. All three roads end at Chilmark Center, where the Corner Way Restaurant and Deli, and Chilmark Store are located. Either establishment contains a wide assortment of lunch choices. Once stocked up with food, your journey to Gay Head lasts only 5 more miles.