Best Trails Near Oak Bluffs MA

Oak Bluffs has 7 trails in the vicinity, including 4 hiking trails and 2 for flatwater kayaking & canoeing. These trails range from 1.3 to 12.6 miles in length. The longest trail in Oak Bluffs is Oak Bluffs to Edgartown Beach Road a well-known trail measuring 12.6 miles in total length.

The most popular trail is Trade Wind Fields Preserve.

More information on the best trails in Oak Bluffs can be found below.
  • Trade Wind Fields Preserve

    0 Reviews

    Oak Bluffs, MA

    For Vineyard locals, Trade Wind Fields is definitely the doggie hangout. For visitors, it is a great place to bring your dog for an afternoon stroll or a morning jaunt. PLEASE NOTE: the airport ...
    •  2 hours
    •  Guide

    For Vineyard locals, Trade Wind Fields is definitely the doggie hangout. For visitors, it is a great place to bring your ...

  • Trade Wind Fields and Farm Pond Preserves - Runway Ramble Trail

    0 Reviews

    Oak Bluffs, MA

    An airport may seem an odd place to take a walk, but lack of development at Trade Wind Fields has preserved the sandplain grassland community, which is fast disappearing elsewhere on the Cape ...
    •  1-2 hours
    •  3.1 miles
    •  Guide

    An airport may seem an odd place to take a walk, but lack of development at Trade Wind Fields has preserved the sandplain ...

  • Lagoon Pond

    0 Reviews

    Oak Bluffs, MA

    If you are looking for a central location to launch your boat or just want a boat to launch, Lagoon Pond is for you. Separated from Vineyard Haven Harbor by a causeway and drawbridge, this deep ...
    •  2 miles
    •  Guide

    If you are looking for a central location to launch your boat or just want a boat to launch, Lagoon Pond is for you. Separated ...

  • Sengekontacket and Trapp’s Ponds

    0 Reviews

    Oak Bluffs, MA

    Sengekontacket, an American indian name meaning “at the bursting forth of the tidal stream,” lies next to Joseph Sylvia State Beach. And Sengekontacket Pond “bursts forth” with much to see and ...
    •  2.5 miles
    •  Guide

    Sengekontacket, an American indian name meaning “at the bursting forth of the tidal stream,” lies next to Joseph Sylvia State ...

  • Trade Wind Fields Preserve

    0 Reviews

    Oak Bluffs, MA

    Take a wide grassy airplane landing field and surround it with woods and a scenic golf course. What do you get? A paradise for dogs and dog walkers. Dogs love the open grassland for chasing balls ...
    •  1.5 miles
    •  Guide

    Take a wide grassy airplane landing field and surround it with woods and a scenic golf course. What do you get? A paradise ...

  • Camp Meeting Grounds

    0 Reviews

    Oak Bluffs, MA

    Now the liveliest island town, with the most nightclubs and fast food shops, ironically, oak Bluffs originated as a place to pray, not play. in 1835, members of the Methodist Church began meeting ...
    •  1.3 miles
    •  Guide

    Now the liveliest island town, with the most nightclubs and fast food shops, ironically, oak Bluffs originated as a place ...

  • Oak Bluffs to Edgartown Beach Road

    0 Reviews

    Oak Bluffs , MA

    This is a great way to start your Martha’s Vineyard vacation. This flat out- and- back ride hugs the eastern side of Martha’s Vineyard, from Oak Bluffs to Edgartown along Beach Road with beautiful ...
    •  12.6 miles
    •  Guide

    This is a great way to start your Martha’s Vineyard vacation. This flat out- and- back ride hugs the eastern side of Martha’s ...