This triangular route is one of the most beautiful family rides on the Vineyard, stopping at some of the most iconic spots on the island. There are bike paths or quiet streets for about 90% of the way, except in downtown Oak Bluffs, which has sidewalks on which to walk your bike. It goes from the Park and Ride lot near the Edgartown “Triangle” shopping area, on the wooded and sandy Beach Rd, along the magnificent Joseph Silvia State Beach (stop for a swim!), up Oak Bluffs’ busy Circuit Ave, through its historic Campgrounds, and returns up County Road to the Edgartown–Vineyard Haven Road. Riding along the E-VH Rd, it then passes 3 beautiful nature preserves (with walking and/or trail biking trails), and back to the Triangle. If there is a strong northerly wind, it might be better to ride this route in reverse, to avoid a headwind on the unsheltered bike path along State Beach.

Distance: 12.1 miles. Elevation Gain: 95 ft.