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Aquinnah Headlands Preserve – West Tisbury loop from Tisbury

Aquinnah Headlands Preserve – West Tisbury loop from Tisbury

Moderate

5.0

(1)

riders

Aquinnah Headlands Preserve – West Tisbury loop from Tisbury

02:36

55.9km

410m

Road cycling

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride. The starting point of the route is right next to a parking lot.

Last updated: October 10, 2025

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Waypoints

Start point

Parking

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13.6 km

Prospect Hill

Nature Reserve

14.6 km

Bliss Pond Farm

Nature Reserve

26.6 km

Gay Head Community Baptist Church

Highlight • Religious Site

Step into history at the Gay Head Community Baptist Church, established in 1693 as the oldest Native American Baptist Church in North America. Originally constructed in 1698 on the Old …

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28.9 km

Aquinnah Headlands Preserve

Highlight • Natural Monument

Aquinnah Headlands Preserve is a beautiful stretch of coastline on the northwestern corner of Martha's Vineyard. The colorful Gay Head Cliffs run along its length, overlooked by Gay Head Cliffs. …

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40.6 km

Chilmark

Highlight • Settlement

Chilmark is a charming, historic town with a lovely center that is home to New England Treasures. It is a lively spot, especially during March when the Martha’s Vineyard Film …

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48.6 km

Dive into the rich history of West Tisbury, a charming New England town settled by English pioneers in 1669. With cute shops, historic buildings, and mills, it's not just a town; it's the island's agricultural heartland.

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55.9 km

End point

Parking

Way Types & Surfaces

Way Types

42.5 km

13.5 km

Surfaces

34.9 km

20.9 km

< 100 m

Elevation

Highest point (60 m)

Lowest point (0 m)

Weather

Today

Friday 21 November

11°C

7°C

0 %

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Max wind speed: 7.0 km/h

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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

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Aquinnah Headlands Preserve – West Tisbury loop from Tisbury

Gay Head Community Baptist Church

Aquinnah Headlands Preserve

Chilmark

West Tisbury

Nearby routes

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