Chilmark Loop

Chilmark, Massachusetts

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This loop highlights the dramatic physical difference in the island towns: from the rolling farmland of West Tisbury to the Vermont-like landscape of Chilmark. With its antique farmhouses, hilly tree-shaded roads, and rural character, Chilmark more closely resembles northern New England than an island resort community. You can go for a workout and complete the trip in two to three hours, or opt for a leisurely day trip with possible stops at any of the six conservation areas and the quaint fishing village of Menemsha to swim, stroll, shop, and sightsee.
Discover Matha's Vineyard

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Discover Matha's Vineyard

by Lee Sinai (Appalachian Mountain Club Books)

This loop highlights the dramatic physical difference in the island towns: from the rolling farmland of West Tisbury to the Vermont-like landscape of Chilmark. With its antique farmhouses, hilly tree-shaded roads, and rural character, Chilmark more closely resembles northern New England than an island resort community.

You can go for a workout and complete the trip in two to three hours, or opt for a leisurely day trip with possible stops at any of the six conservation areas and the quaint fishing village of Menemsha to swim, stroll, shop, and sightsee.

©  Lee Sinai/Appalachian Mountain Club Books. All Rights Reserved.

Activity Type: Road Biking
Nearby City: Chilmark
Distance: 34.5
Trail Type: Loop/Lollipop
Skill Level: Moderate
Season: Best Spring through Fall
Driving Directions: Directions to Chilmark Loop

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May 2018