Oak Bluffs, MA Trails and Parks

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 most popular trail is Trade Wind Fields Preserve.
  • Trade Wind Fields PreserveView Trail Details

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    Oak Bluffs, MA

    • Hiking  
    •  2 hours
    •  Guide

    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 ...

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

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    Oak Bluffs, MA

    • Hiking  
    •  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 grassland community, ...

  • Lagoon PondView Trail Details

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    Oak Bluffs, MA

    • Flatwater Kayaking & Canoeing  
    •  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 from Vineyard ...

  • Sengekontacket and Trapp’s PondsView Trail Details

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    Oak Bluffs, MA

    • Flatwater Kayaking & Canoeing  
    •  2.5 miles
    •  Guide

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

  • Trade Wind Fields PreserveView Trail Details

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    Oak Bluffs, MA

    • Hiking  
    •  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 for dogs and dog walkers. ...

  • Camp Meeting GroundsView Trail Details

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    Oak Bluffs, MA

    • Hiking  
    •  1.3 miles
    •  Guide

    Now the liveliest island town, with the most nightclubs and fast food shops, ironically, oak Bluffs originated as a place to pray, not play. ...

  • Oak Bluffs to Edgartown Beach RoadView Trail Details

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    Oak Bluffs , MA

    • Road Biking  
    •  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 Vineyard, from ...