Menemsha Hills
Chilmark, Martha's Vineyard, MA
211 acres
Bird Watching Hunting Mountain Biking Not Permitted Fishing Walking/Hiking (Moderate) Picnicking Dog Walking Not Permitted Quest

About Menemsha Hills

Experience the drama of a rocky shoreline and scenic vistas across Vineyard Sound to the Elizabeth Islands from the second-highest point on the island.

What makes Menemsha Hills Reservation a special place?
We think it’s the variety of habitats – and range of activities – to be enjoyed within this 211-acre preserve. Climb to the top of the second-highest point on the Vineyard. Enjoy a leisurely picnic. Take in some spectacular ocean views, then take fishing rod in hand for some surfcasting. (Or just get away from it all on a quiet woods trail.)

Wet, Dry, then Very Wet
The three miles of trails allow walkers to experience multiple mini-environments, including wetlands; woodland groves leading to a hilltop; open, wind-blasted coastal plain; and a rocky ocean edge. The low, marshy areas just beyond the parking areas support red maples and beech, while red, white, and black oaks mantle the slopes of Prospect Hill. Approaching the shore, dune grass and pitch pine predominate. Look for goldenrod and beach plum helping to anchor the dune cliffs above the beach, where rocks of every size dot the sand and line tide pools.

High and Mighty
At 308 feet in elevation, Prospect Hill is the second highest point on the Vineyard (at 311 feet, Peaked Hill, located just southeast, takes top honors.) Along the path, pass holly and high-bush blueberry, which thrive in the sandy, moist soils here. From the top of the aptly-named hill, the prospects are indeed delightful, a panorama extending from the Elizabeth Islands, past pretty Menemsha and the cliffs of Aquinnah, to Noman’s Island.

The Age of Ice
This reservation (and all of Martha’s Vineyard and the other islands and coastal areas of the Northeast), was crushed and scraped, carved and shaped, by thousands of years of glacial advance and retreat. The wetlands here exist partly as a result of their underpinnings of impervious clay, created when looser sand and gravel soils were compressed by millions of tons of ice.

Within the woods, there are still some sizeable boulders, called erratics, left behind by the retreating ice. (Many were hauled from their earthen beds to be used in breakwaters). Similarly, the uplands and bluffs overlooking Vineyard Sound were formed as the glacier creaked and rumbled across this corner of the North American continent.

Hike to one of the highest promontories on the island, then descend through woodlands and hardy seaside groundcover to coastal bluffs overlooking Vineyard Sound, where visitors can enjoy sublime with views of the Elizabeth Islands.

Bricks by the Brook
Although early Vineyard commerce generally revolved around fishing, seafaring and farming, heavier industry also played a part in the island’s history. Just beyond the northeast edge of this property, along Roaring Brook, stands the remnants of a brick chimney, all that remains of a 19th-century brickworks.

Moderate hiking along three miles of trails. The spur to top of Prospect Hill may require minor exertion.

When to Visit
Open year-round, daily, sunrise to sunset. Allow a minimum of 1½ hours.

Seasonal portable toilets at parking lot.

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Regulations & Advisories

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Deer hunting allowed with written authorization from The Trustees of Reservations. For more information, please contact the Martha’s Vineyard Regional Office at 508.693.7662.

The Trustees reserves the right to photograph or video visitors and program participants for promotional use, and usage of our properties implies consent. Find the full policy here.


North Road
Chilmark, MA 02535
Martha's Vineyard
Telephone: 508.693.3678

Latitude: 41.3645
Longitude: -70.7422

Get directions on Google Maps.

From State Rd. in West Tisbury, turn right onto North Rd. west toward Chilmark and follow for 4.7 mi. Entrance and parking (20 cars) are just past Tabor House Rd. on right.


When to Visit
Open year-round, daily, sunrise to sunset. Allow a minimum of 1½ hours.

FREE to all.

Property History

Property Acquisition History
Original acreage a gift of Nathaniel L. and Catherine P. Harris in 1966 in memory of Nathaniel and Sarah A. Harris. Additional land given by Mrs. David J. Epstein in 1980, and by the Prospect Hill Association in 1988.


The Menemsha Hills Quest
A quest is an educational treasure hunt and outdoor experience that involves answering questions, using map skills, and deciphering clues that will lead to a hidden “treasure” box. This is an independent, self-guided adventure. Wear sturdy shoes and bring water. Compass and Quest booklets are available at the property.

  • Duration: 3 – 4 hours
  • Days/Times: Daily, sunrise to sunset.
  • Reservations: First come, first served.

Claire Saltonstall Education Program
The Claire Saltonstall Education Program offers activities for Martha's Vineyard school children throughout the year. For more information, contact Trustees Education and Interpretation Program Coordinator Molly Peach at

We just posted a StoryWalk® at Menemsha Hills Reservation! A StoryWalk® is a wonderful way to get children, families, and adults outside! We’ve taken a Vineyard-based children’s story (No Turn For Tern! A Martha's Vineyard Moonlight Mystery by Rebecca J. Loescher, illustrated by Judith Pfeiffer) and posted the pages along the Menemsha Hills trail. The individual storybook pages lead visitors along the trail, ultimately reaching the second highest place on the island: Prospect Hill!  
We're looking forward to many island residents and visitors alike experiencing our StoryWalk® this spring and summer. We'll be changing the book periodically throughout the varying seasons.
The StoryWalk® Project was created by Anne Ferguson of Montpelier, VT and developed in collaboration with the Vermont Bicycle & Pedestrian Coalition and the Kellogg Hubbard Library.

2015 Martha's Vineyard Tour Brochure >>

Conservation and Stewardship

Management Planning for Our Properties

Since 1891, The Trustees of Reservations have worked to protect special places in Massachusetts and maintain them to the highest standards. To ensure these standards are met, a program of careful planning and sound management is essential. Comprehensive property management plans are created for each reservation and are completely updated approximately every ten years. We often work with volunteers, property users, and members of the community to carry out this planning, which typically involves several steps:

  • Describing in detail the site’s natural, scenic, and historical resources; identifying management issues related to the protection of those resources. 

  • Describing how visitors use the property; outlining the opportunities that the property provides for people to become involved in the work of conservation and caring for their community.

  • Developing a detailed list of management recommendations, a work plan, and a description of financial needs for implementing the actions.

  • Developing a prescribed routine management program for the reservation that will guide staff work plans, volunteer involvement, and the allocation of human and financial resources.

Maps and Resources

Printed trail maps are distributed free from bulletin boards in parking areas. Please understand that supplies periodically run out. We recommend downloading a trail map before you visit. Some publications are also available for purchase at the Islands Regional Office, 860 State Road, Vineyard Haven (508.693.7662).

Planning Your Visit

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Before You Go
We encourage you to visit as many Trustees properties as you can.

Wherever your travels take you, please observe all posted regulations, follow special instructions from property staff, and keep in mind the Stewardship Code:

  • Protect wildlife and plants.
  • Guard against all risk of fire.
  • Help keep air and water clean.
  • Carry out what you carry in.
  • Use marked footpaths and bridle paths.
  • Leave livestock, crops, and machinery alone.
  • Respect the privacy of neighboring land.
  • Enjoy and share the landscape with others.

Click on links below for further visitor information:

Before Setting Out

Enjoying Trustees Reservations


About Hunting on Trustees of Reservations Land