I first explored Menemsha Hills more than fifty years ago, when the trails we followed were mostly made by cattle and deer. In the early 1940s, my father, with the aid of friends, had stacked a pile of boulders on the summit of Prospect Hill. His goal was to make the top of the pile roughly three feet higher than the 311-foot Peaked Hill, which is the Island’s highest point. I still to this day climb on top of that pile of boulders just to get the feeling of knowing that nobody is standing higher than me on the Vineyard.

A Scottish friend of mine said the land reminded him of Scotland in miniature, with the wide-open vistas, the rocky shoreline, and the sight of fishing boats motoring on Vineyard Sound. I love to go there with family and friends, but just as often, I hike alone with my camera and photograph the beauty this place holds, with its birds, marshes, stone walls, and hilltop vistas of Vineyard Sound, the Elizabeth Islands, Menemsha, and the Gay Head Light flashing its red and white beacon in the far-off distance.

Thanks from a grateful Island

In 1867, Boston businessman Nathaniel Harris bought the sprawling Smith and Barrows brickworks and adjacent highlands from which clay and other raw materials were mined. In its heyday, as many as 600,000 bricks a year were loaded onto ships from long piers off the rocky shore, and incorporated in buildings in Boston, New Bedford, and elsewhere. But with firewood for the kilns dwindling, the brickworks closed in the late nineteenth century. In 1966, the Harris family gave the bulk of the property to The Trustees of Reservations for the benefit of all. Later donations by Mrs. David J. Epstein, also a member of the Harris family, and the Prospect Hill Association brought the total of today’s preserved land to 211 acres.

Lay of the Land

Three miles of trails wind through low-lying wetlands, moss-covered woodlands, and crooked beetlebung groves. Make your way past small tadpole-filled ponds, bass-blitzing rocky beaches, and up to stunning overlooks with unparalleled views of the north shore. Prospect Hill is a great spot for picnicking and sunset genuflecting, with a view to the west that includes all of Aquinnah and most of Menemsha Pond. The top of Great Sandy Bank has equally remarkable views along the rocky coastline of the north shore, including the dilapidated chimney from the old Harris brick factory.

Practically Speaking

The reservation is open year-round from dawn to dusk. The parking lot has trail maps and a portable restroom. I suggest hiking boots, water, a snack, binoculars, bug spray, a cell phone, and flashlight if you plan to watch the sunset. Rugged baby strollers are manageable on the trails. The walk back to the parking lot from the beach is a good workout because it’s mostly uphill. I usually notice my heart rate is up by the time I return. For more information and a downloadable trail map, visit thetrustees.org.