One of the best waterfront runs on the Vineyard is along East Chop Drive, in Oak Bluffs. Great combination of waterfront running, classic homes, and a sense of quaint Oak Bluffs. Start at the Oak Bluffs ferry terminal, enjoy the Harbor, and head out Lake Ave. From there, the route travels through the quiet but residential East Chop Dr. with views of the ocean as well as gorgeous beachfront homes. Passing by the East Chop Lighthouse at Telegraph Hill is one of the highlights. Caution: There are no sidewalks or shoulders for the majority of this loop. However, in high season, there’s a ~1 mile section closed off to cars and a dedicated lane for pedestrians/cyclists.
E. Chop ends at about the 2 mile mark at the intersection with Temahihan Ave. & New York Ave. and turns inland. So you can do a there and back, or run back to Oak Bluffs center via New York Ave. , which cuts about 1/2 mile off the route. Or, add to the return by enjoying some of the pleasant interior streets of Oak Bluffs inside of New York Ave.
For a longer run, continue toward Vineyard Haven using Beach Rd. — it’s another 1.7 miles one-way.