Waskosim’s Rock Reservation

Much variety here: woodlands in the reservation’s southerly end segue into open fields — some high and some low — in the middle tier and these, finally, segue into deeply shaded wetlands along the Mill Brook at the northerly end. Remnants of the 17th century homestead of James Allen, the first patentee of Tisbury, are found in the fields: a capstone over an abandoned well, a cellar hole, stone stairs, a paddock, all in various states of desuetude. Eerily perched atop one of the ridges is the Waskosim’s Rock itself, a boulder whose shape and location have long figured in Wampanoag and more recent island history. The rock marked the beginning of the “Middle Line,” a stone wall boundary running to the Menemsha Pond in order to separate English and Wampanoag lands in the mid-1600s.

• Difficulty rating: Difficult
• Trail: UA Parking located at the end of Mill Brook Road which is located off Old Farm Road.
• Points of Interest: Access to meadows, old stonewalls, and the site of land bank goat grazing
• Benches: 1