A variety of habitats emerge along former woods roads and footpaths through this 211-acre preserve. The popular Harris Trail loops through perched wetlands as it leads to Prospect Hill, the second-highest point on the island, which affords spectacular views of the Menemsha harbor entrance, the Elizabeth Islands, and Gay Head Light. At Menemsha Hills’ bluffs, take in a view from the top of the Great Sand Bank that provides a stark reminder of the Vineyard’s glacial origin. You can also visit the remains of a 19th-century brickyard on Roaring Brook (see The Brickyard, page 188).

Discover the many treasures of Menemsha Hills—meander through Black Tupelo (“Beetlebung”) and oak forest, witness the views from the Great Sand Overlook, and enjoy the beauty of the island’s rocky north shores.

Hike three miles of trails past holly, high-bush blueberry, and more than a few boulders and glacial erratics. Follow the Harris Trail to the top of the hill, which affords spectacular views of the Menemsha harbor entrance, the Elizabeth Islands, and Gay Head Light. Descend through the woodlands and hardy seaside groundcover to coastal bluffs overlooking Vineyard Sound to the rocky north shore beach—possibly one of the quietest seaside landscapes on the island—and enjoy the view or cast a line. Continue your hike to the historic Brickyard.

When To Visit
Daily, sunrise to sunset. Allow a minimum of one and a half hours.

Admission
FREE to all.

We welcome school and youth groups for experiential educational programs. Please visit our Education Page for details and to initiate a visit request.

North Road
Chilmark, MA 02535

Get directions on Google Maps.

From State Rd. in West Tisbury, turn right onto North Rd. west toward Chilmark and follow for 4.7 mi. Entrance and parking (20 cars) are just past Tabor House Rd. on right.

The property offers a portable toilet, bike racks, and benches along the trails.

To view or download a trail map, click here.

• Bikes and horseback riding not permitted, year-round.
• Our trail system runs through several unique and fragile habitats. Please help us preserve these valuable ecosystems and hike only on designated trails.
• Poison Ivy and ticks are abundant along trail edges.
• Authorized seasonal hunting is allowed on this reservation with written permission for a limited number of hunters through a deer management program administered by The Trustees. Per MassWildlife regulations, hunting is permitted from the first Monday in October through December each year, from ½ hour before sunrise all day until ½ hour after sunset, Monday through Saturday. Hunting is not allowed on Sundays. Signage is posted at the property listing safety precautions and requirements. Learn more about hunting on Trustees properties. Any questions may be directed to The Trustees at Info@TheTrustees.org.
• PHOTOGRAPHY: We ask that photographers or their clients become Contributing Level Members before conducting portrait sessions at this property. Click here for more information, and to request permission for any portrait sessions. The Trustees of Reservations reserves the right, and may give permission to its designated photographers and videographers, or to outside media, to photograph or video visitors and program participants at all its facilities and properties.