Waskosim’s Rock Reservation

Chilmark, Massachusetts 02552

Waskosim’s Rock Reservation

Waskosim’s Rock Reservation Professional Guide

Detailed Trail Description from our Guidebook

"Waskosim’s rock reservation offers well-maintained trails that wind through varied terrain filled with a mix of wildflowers, birds, and trees. The reservation is named after an immense boulder that dominates one of the highest hills on the Vineyard. A huge crack running down the middle of Waskosim’s rock has inspired numerous local legends and created many photo opportunities.

The reservation is located off the left side of North Road 1.5 miles west of the junction with State Road, and just after the Chilmark town line sign."

More Waskosim’s Rock Reservation Professional Guides

Detailed Trail Descriptions from Our Guidebooks

"This reservation is named for a huge glacial boulder that once served as a benchmark for establishing the boundary between lands of the native Wampanoags and property claimed by English settlers. Many trails, generally in the form of three loops, crisscross the hilly terrain, which is divided between woodland and meadow. Note: Trail names (colors) on the latest Land Bank map may not correspond in all cases to signage or to names on older maps."

Waskosim’s Rock Reservation Trip Reports

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Hike that gives one an interesting look at the Island's interior. We entered at the parking area, and once on the trail, took our first left along a brook and with a mild climb came to Waskosim's Rock. Some nice overlooks along the soft and generally well-marked trails. Far off views of Vineyard Sound. We looped back along the trails and without using a map, were able to easily return to the parking lot after about an hour and a half.

Waskosim’s Rock Reservation Photos

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Trail Information

Nearby City
Trail Type
Skill Level
Best Spring through Fall

Trail Log