Waskosim’s Rock Reservation

Walk through remnants from the human and geological history of Martha’s Vineyard at Waskosim’s Rock Reservation, which is located at the West Tisbury-Chilmark town line. With its mix of open meadows, gentle woodland paths and sweeping ridge-line views, visitors will find a variety of adventures at this Martha’s Vineyard Land Bank Commission property.


Visitors to Waskosim’s Rock Reservation travel through Martha’s Vineyard’s past as they traverse its trail. Evidence of the island’s geological origins are strewn across the property–large boulders dropped as the glaciers retreated. The reservation’s namesake is just one of a number of glacial erratics perched atop a ridge that offers sweeping views from Vineyard Sound to the middle of the island.

Waskosim’s Rock also figures in Native American and colonial history. The boulder served as a landmark for the Wampanoag people and later marked the “Middle Line,” a stone wall boundary running to the Menemsha Pond in order to separate English and Wampanoag lands in the mid-1600s. In the open meadows below the rock, you will see long stone walls and the remains of what was the 17th century homestead of James Allen, the first patentee of Tisbury, including a cellar hole, stone stairs, and a paddock.

The reservation is popular not only with hikers, dog walkers, and birdwatchers, but also with mountain bikers. The property offers a good deal of diversity from the wooded wetlands that border Mill Brook to open fields and the forests that cover its southerly end, where it connects with Tiasquam Valley Reservation.


The trail system at Waskosim’s Rock Reservation covers roughly three miles, wending its way from woods and wetlands to open fields and ridges. Starting from the parking area at North Road, the path begins gently, crossing Mill Brook and looping through woods and wetlands. At the first intersection, turn left for the quickest route to the open fields of Allen’s former homestead and Waskosim’s Rock.

From the open fields, trail signs point the way to Waskosim’s Rock, offering several routes up the steep ridge on which it sits. Once you climb the ridge, you will pass a handful of large glacial erratics before reaching the reservations’ namesake, which is perched on a hillside among a small grove of oaks and pines.

Beyond the rock, the trail system loops around the ridge to the fields and the Mill Brook loop while another path to the left continues south to another loop through woodlands and a spur that connects to the Tiasquam Valley Reservation.

Habitats & Wildlife

Waskosim’s Rock Reservation sprawls across the ridges and valley that the glaciers left on the western side of Martha’s Vineyard. It harbors a variety of habitat. From the trailhead, you will pass through lush wetlands that green up early in spring with skunk cabbage and spacious woodlands of oaks, maple, white pine, and holly. Grassland habitat covers the open meadows, providing fertile hunting grounds for red-tailed hawks that can often be seen soaring overhead.

Property Owned By

The land bank is an independent public authority dedicated to preserving open space for the benefit of the entire Martha’s Vineyard community.

Size: 185 acres
Hours: Sunrise to sunset
Parking: Medium-sized dirt parking area
Cost: Free
Trail Difficulty: Easy, Intermediate
Dogs: Yes, on leash
Facilities: None
ADA Accessible: No

Please follow all posted rules and regulations at this property.

Address & Contact Information
10 North Road
Chilmark, MA 02535
41.398216, -70.705384
Martha's Vineyard Land Bank Commission: 508-627-7141
Email: mhill@vineyardlandbank.com

Please follow all posted rules and regulations at this property.

Waskosim’s Rock Reservation
Chilmark, MA
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Sun, August 18
Woods Hole to Falmouth Heights,
Buzzards Bay Watershed Ride
Sun, October 06
Sakonnnet Point to Woods Hole,

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Waskosim’s Rock Reservation

The mix of open meadows, woodland paths, and sweeping ridge-line views at Waskosim's Rock Reservation make it a fascinating place to visit and re-visit.