Perched high on the ridge between Chilmark and West Tisbury, Waskosim’s Rock is one of Martha’s Vineyard’s most quietly powerful places — a vast, preserved landscape where stone walls, wild meadows, and glacial boulders tell stories that stretch back thousands of years.
For locals, it’s a favorite trail and picnic spot. For historians and conservationists, it’s a landmark of resilience — both natural and cultural.
A Rock Shaped by Ice and Time
Long before Martha’s Vineyard was an island, glaciers carved, carried, and deposited stones across this landscape. Waskosim’s Rock, a dramatic glacial erratic, was left behind some 15,000 years ago — a massive granite boulder that now anchors the ridge and lends the reservation its name.
Over time, the rock became a natural gathering point — first for the Wampanoag people, then later for settlers, farmers, and modern-day hikers who find inspiration in its weathered form and panoramic views.
A Boundary Between Two Worlds
In the 1600s, as colonial settlement took root on the Vineyard, Waskosim’s Rock marked an important boundary line between Wampanoag land and early English farms. The “Middle Line,” as it was called, ran from the rock down toward Menemsha Pond, dividing tribal and colonial territories.
The word Waskosim itself is believed to derive from a Wampanoag term meaning “new stone.” To this day, the site carries a quiet sense of reverence — both a natural monument and a reminder of the Island’s deep Indigenous history.
Echoes of the Colonial Era
As you walk the trails today, the remnants of 17th- and 18th-century farming still surface. Stone walls, cellar holes, old stairways, and the remains of the James Allen homestead — the first English patentee of Tisbury — still mark the land.
Here, open pastures have slowly reclaimed themselves, the forest grown back over long-abandoned sheep fields. The rhythm of human use and natural renewal plays out visibly across the terrain.
Saving Waskosim’s: A Community Victory
In the 1980s, development pressures nearly changed this landscape forever. Plans surfaced for dozens of house lots across the surrounding acreage.
Instead, the newly formed Martha’s Vineyard Land Bank — established in 1986 with a 2% real estate transfer tax dedicated to conservation — stepped in. By 1990, Waskosim’s Rock had become one of the Land Bank’s first major acquisitions, ensuring that the area would remain forever open to the public.
That act of preservation wasn’t just about protecting one property — it set the tone for how the Vineyard would define its values: prioritizing open space, natural beauty, and cultural heritage over unchecked growth.
The Experience Today
Today, Waskosim’s Rock Reservation encompasses 185 acres of protected land. Managed by the Land Bank, the trails wind through woodlands, wetlands, meadows, and over Mill Brook before rising to the ridge where the rock rests.
From the top, the views stretch over Vineyard Sound, Chilmark’s hills, and the forested lowlands below — one of the most rewarding vantage points on the Island.
Wildlife is abundant, the trails are gentle, and in every season, there’s a sense of calm that feels distinctly Vineyard: elegant, unspoiled, and enduring.
Why It Matters
For those who know Martha’s Vineyard, Waskosim’s Rock represents something more than a trailhead or a scenic overlook. It’s a living emblem of what makes the Island extraordinary — its layers of history, its devotion to preservation, and its reverence for the land itself.
To walk here is to step into the Vineyard’s story — from glacial beginnings to modern stewardship — and to feel a connection that transcends time.
