Outbound Collective logo

Hike Menemsha Hills Reservation Loop

Chilmark, Massachusetts

based on 1 reviews



3.5 miles

Elevation Gain

295 ft

Route Type



Added by Natalie O'Connor

Off-season activities are hard to come by on Martha's Vineyard. This short hike will lead to breathtaking views of Vineyard Sound and if you're lucky, sightings of a small herd of fluffy white tail deer!

GPS service in densely wooded areas on the Vineyard is hard to come by, so plugging in Menemsha Hills Reservation before getting on the road is advised. Traveling down N Road, you'll find an unmarked gravel road located between Turtle Cove and Trustees Lane. A short 400 meter drive will take you around to a small parking lot and the trailhead. Signage and maps clearly mark the area.

Totaling just over 3 miles, this portion of the Hills consist of Harris Loop and Nashawakemuck Loop. If you're really here for the viewpoints, I recommend entering the trailhead and veering left. This will lead you about a half mile before hitting the fork, stay left to wander up to Prospect Hill or to reach Nashawakemuck Loop. 

The next fork, stay right to continue on your viewpoint tour. The first viewpoint will be on the left. A tree filled patch opens up to the beautiful blue Sound. A permanent bench gives you the opportunity to take a breather while taking in the view. Should weather permit, this would be a great area for a picnic.

Another 3/4 mile leads you to a short, sandy jaunt to a breathtaking view of Vineyard Sound and the Elizabeth Islands. You'll also have the opportunity to get a glimpse of a few large ocean front properties which are usually only visible from the water.

Turn around and head back the way you came, or perfect your figure 8 skills by looping around the portions of the trails you skipped on your way in.

Note: This is not a pet friendly adventure.

Read More

Download the Outbound mobile app

Find adventures and camping on the go, share photos, use GPX tracks, and download maps for offline use.

Get the app


Easy Parking
Family Friendly


Leave No Trace

Always practice Leave No Trace ethics on your adventures and follow local regulations. Please explore responsibly!


Photograph Lambert's Cove

Hike Huckleberry Barrens Trail

Visit Edgartown Lighthouse

Hike Frank Knowles–Little River Reserve Trail

Hike Gooseberry Island

Birdwatch at Sachuest Point