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Menemsha Hills Reservation. Menemsha Hills Reservation has 4 miles of some of the most challenging, steep, and breathtaking hiking trails on the island, including a stroll up to Martha's Vineyard's second-highest point and another ramble that descends down through the windswept valley to boulder-strewn Vineyard Sound Beach. North Rd., Menemsha, MA, 02552. www.thetrustees.org.