Martha's Vineyard, MA

Oak Bluffs Running Tour

This is a ‘runseeing’ tour of Oak Bluffs, combining history, beautiful residential areas, and sections along the water. We’ve designed a couple of routes, but also good to come up with your own. The highlights of a tour of Oak Bluffs incorporate Flying Horses Carousel/Circuit Ave. commercial area, a tour of Ocean Park, a jaunt along Seaview Ave., and a loop around the gingerbread houses of the Martha’s Vineyard Camp Meeting Association.

Short run – 3 miles: A good place to start is at the Flying Horses Carousel. Do a 1/4 mile tour of the marina, near the ferry terminal, and then another 1/2 mile around the perimeter of Ocean Park. Then there are a couple of options. For the shorter, ~3 mile run, head out Seaview Ave., with great water views, and then take Nantucket Ave., by Waban Park, to Circuit Ave. (Note there’s a separate pedestrian path along Oak Bluffs Harbor, paralleling Circuit Ave. extension and Lake Ave.) Head down Circuit Ave., one of the main commercial streets in Oak Bluffs, back toward the water, and do a quick 1/2 mile tour around the gingerbread houses of the Martha’s Vineyard Camp Meeting Association.

Longer Run – 5-9 miles: For a nice add-on, run further out Seaview Ave. and along the Tradewinds Preserve trails (part of the Land Bank Trails), for about 1 mile, which includes a jaunt along the Farm Neck Golf Club. For the 9-mile version, do the 4 miles out and back on East Chop, which is some of the nicest waterfront running on the Vineyard, with ocean views and spectacular homes!

Oak Bluffs Walking Tour Highlights
  • Short run: 3 miles. Longer run: includes Land Bank Trails: 5 miles; includes East Chop 9 miles
  • Short run: 50 feet; Long run: 100 feet
  • Flying Horses Carousel, or anywhere central in Oak Bluffs
  • Oak Bluffs is seved by the VTA