The 6.3 mile Cross-Oak Bluffs trail begins where the Cross-Tisbury ends: at Four Corners where the Greeenlands property meets the State Forest paved bike trail.  It takes a peaceful detour along a field path called “Tiny Meadow” and then heads north, past Goodale’s Pit, across the Vineyard Haven-Edgartown Road and onto the Olds Holmes Hole Road.  It then goes almost immediately left on the “Old Back Road” through the Southern Woodlands and beyond.  It goes east along Pennsylvania Avenue and onto the County Road.  

From there, it picks up paths through Trade Winds, past the back of the Oak Bluffs School and onto Farm Pond Preserve.  At South Circuit Avenue, go right and then take Naumkeag Avenue until it ends at Ocean Park.