Vineyard Up Island Tour

Tisbury, Massachusetts 2573

Vineyard Up Island Tour

Vineyard Up Island Tour Professional Review and 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 downtown areas. See the Gay Head Cliffs and Lighthouse in Aquinnah, ride through rural farmland in Tisbury, take the Menemsha Bike Ferry and ride through Chilmark and West Tisbury to Oak Bluffs. Complete the loop by adding Ride 39 around East Chop back to Vineyard Haven.

This is the second- longest ride in this guidebook after Ride 29 (Grand Tour of the Outer Cape), and will take you through every one of Martha’s Vineyard’s six towns: Tisbury (Vineyard Haven is not a town, although most everybody traveling here seems to think so), West Tisbury, Chilmark (including Menemsha), Aquinnah (formerly called Gay Head but changed to its original Wampanoag name by a popular vote of 79 to 21 in 1997), Edgartown, and Oak Bluffs. This ride focuses on mostly the western half of the Vineyard, with a lot of time spent passing sheep, cows, and horses, but also with fabulous views of the ocean and other waterways connecting various parts of the island. And it’s a leg- burner with its numerous hilly sections."

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Trail Information

Nearby City
Trail Type
3-4 hours
Riding Time
Arrow Street Atlas: Cape Cod including Martha’s Vineyard & Nantucket, p. 98
Local Maps

Activity Feed

Nov 2018