Best Trails Near Tisbury MA

Tisbury has 9 trails in the vicinity, including 4 for road biking and 3 hiking trails. These trails range from 1.1 to 46.4 miles in length. The longest trail in Tisbury is Vineyard Up Island Tour a well-known trail measuring 46.4 miles in total length.

The most popular trail is West Chop Woods - Woodsy Walk Trail. Trails.com member Alexander M. recently completed West Tisbury South Loop.

More information on the best trails in Tisbury can be found below.
  • West Chop Woods - Woodsy Walk Trail

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    Tisbury, MA

    This 85-acre sanctuary, owned by the Sheriff’s Meadow Foundation, provides a swath of wooded open space in an otherwise-developed, mostly residential area. Old Lighthouse Road, a dirt road, bisects ...
    •  1 hour
    •  1.6 miles
    •  Guide

    This 85-acre sanctuary, owned by the Sheriff’s Meadow Foundation, provides a swath of wooded open space in an otherwise-developed, ...

  • Tisbury Meadow Preserve - Esker Escapade Trail

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    Tisbury, MA

    This easy walk has something for everyone. Geology buffs will enjoy strolling atop an esker, which is a sand and/or gravel ridge formed by the movement of water associated with a melting glacier. ...
    •  1 hour
    •  1.5 miles
    •  Guide

    This easy walk has something for everyone. Geology buffs will enjoy strolling atop an esker, which is a sand and/or gravel ...

  • Ripley’s Field Preserve - Forest and Field Foray Trail

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    Tisbury, MA

    This easy, well-shaded walk wanders through Ripley’s Field, a lovely meadow graced by an old windmill and wildflowers in season, and then follows the 56-acre preserve’s perimeter through a forest ...
    •  1 hour
    •  1.1 miles
    •  Guide

    This easy, well-shaded walk wanders through Ripley’s Field, a lovely meadow graced by an old windmill and wildflowers in ...

  • Lake Tashmoo

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    Tisbury, MA

    For a preview of coming attractions, stop at the Lake Tashmoo overlook on State road in Vineyard Haven to watch boats motoring in and out of Vineyard Sound. From this picture-postcard setting, ...
    •  1.4 miles
    •  Guide

    For a preview of coming attractions, stop at the Lake Tashmoo overlook on State road in Vineyard Haven to watch boats motoring ...

  • Wapatequa Woods Reservation to Tisbury Meadow Preserve

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    Tisbury, MA

    Easy to access and fun to ride, these two Land Bank properties include typical Vineyard woodlands, ancient dirt roads, and a large meadow. if you are in need of an energy boost, you can stop ...
    •  4 miles
    •  Guide

    Easy to access and fun to ride, these two Land Bank properties include typical Vineyard woodlands, ancient dirt roads, and ...

  • West Tisbury North Loop

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    Tisbury, MA

    If you seek a rural experience but don’t have time for an up-island ride, try this short loop. rolling country roads, picturesque ponds for cooling off, and several hiking and off-road options ...
    •  13.4 miles
    •  Guide

    If you seek a rural experience but don’t have time for an up-island ride, try this short loop. rolling country roads, picturesque ...

  • West Tisbury South Loop

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    Tisbury, MA

    Take a trip back in time to when the Vineyard relied more on farming than tourism, by cycling through the agrarian center of the island, West Tisbury. This ride also offers opportunities for ...
    •  25 miles
    •  Guide

    Take a trip back in time to when the Vineyard relied more on farming than tourism, by cycling through the agrarian center ...

  • Oak Bluffs–East Chop–Vineyard Haven

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    Tisbury, MA

    Do it as an out- and- back or combine with Ride 38 to see the rest of the island. Beautiful views of Vineyard Sound and Falmouth, riding the East Chop to the lighthouse. Explore Oak Bluffs and ...
    •  10 miles
    •  Guide

    Do it as an out- and- back or combine with Ride 38 to see the rest of the island. Beautiful views of Vineyard Sound and Falmouth, ...

  • Vineyard Up Island Tour

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    Tisbury, MA

    Tour every town on Martha’s Vineyard and get a taste of what the rest of island is like, away from the touristy, bustling downtown areas. See the Gay Head Cliffs and Lighthouse in Aquinnah, ride ...
    •  46.4 miles
    •  Guide

    Tour every town on Martha’s Vineyard and get a taste of what the rest of island is like, away from the touristy, bustling ...