Take a Hike on These Wonderful Hamptons Walking Trails

Montauk Point Lighthouse
Montauk Point Lighthouse, Photo: Stephanie Kossman

“Only ideas won while walking have any value.”
—Friedrich Nietzsche

According to the Mayo Clinic, the health benefits of walking are plentiful and include maintaining a healthy weight, preventing or managing various conditions—including heart disease, high blood pressure and type 2 diabetes— and increasing and improving bone and muscle strength, mood, balance and coordination. Getting a good walk can also do wonders for the walker’s mental health. Walking has proven to improve self-perception and self-esteem, mood and sleep quality, and to reduce stress, anxiety and fatigue. It also clears the head, working out and clearing old ideas and making way for new ones. Any time not spent in front of the blue light of computer, television or smartphone screens is time well spent. And, yes, the East End has lots of places one can go to have a good walk.

The East Hampton Trails Preservation Society (EHTPS) maintains a series of trails throughout East Hampton Town. Perhaps the most remote and interesting is a three-mile self-guided tour through the abandoned Northwest Settlement know affectionately as the East Hampton Ghost Town. According t0 Lee Dion’s write-up of the Ghost Town on the EHTPS website, East Hampton Town records of 1653 speak of, “A cartway to ye Northwest meddow,” which settlers followed in order to gather salt, hay and seaweed that was used for insulation, fertilizer and cattle bedding. Northwest eventually became East Hampton’s earliest port and the first merchant ship landed there, from Boston, in 1665.

By the time the 18th century rolled around, the area contained 15 large farms, a mill, wharves, warehouses, a pest house (a shelter for those with contagious diseases), a fish factory, a sawmill and, according to the trustee journals, a shipbuilding enterprise. A public school operated in the area from 1792 until 1885. According to Dion, Northwest Harbor flourished from 1653 until 1761 and lasted until 1885.

There are 15 points of interest on this hike, including the former property of obstinate Irishman Josiah Kirk who sued the Town over seaweed rights. He won the case, but it cost him everything he owned and he died destitute at an almshouse in Yaphank. Other highlights include sweeping water views, one with Cedar Point Lighthouse in the background and another with Barcelona Neck in the background and Sag Harbor barely visible in the distance. If you’re going to take this walk, bring enough water to keep you hydrated and visit ehtps.org/lost-ghost-town to download a map, guide, and Dion’s history of the place.

For a more somber walking spot, and someplace to escape the coming summer crowds if need be, visit Oakland Cemetery in Sag Harbor. Founded in 1840, Oakland currently sits on 26 acres and is the permanent resting place of over 4,000 people, including more 18th- and 19th-century sea captains than in any other Long Island cemetery. Among the treasures in Oakland is the Broken Mast Monument, which commemorates all the whalers “Who periled their lives in a daring profession and perished in actual encounter with the monsters of the deep.”

The long, mostly flat rows offer a quiet place to reflect while paying your respects to some members of the oldest families on the East End and many other historically significant individuals. Writers Nelson Algren, William Gaddis, Spalding Gray, Prentice Mulford and James Salter are all buried there. So are local astronomer, clockmaker, scientist and bookbinder Ephraim Byrum (whose historic house is next door), founder of the New York Ballet, George Balanchine, U.S. diplomat Richard Holbrooke, artists Hans Namuth, Val Telberg and so many more.

For a bit of a more touristy, sightseeing—and perhaps more strenuous—walk head out to Montauk Point before the traffic doubles your travel time. A great walk starts just north of the Montauk Point Lighthouse. There’s a dirt path that leads down to the beach. Once you’re down at the water, relax, take a deep breath and soak up the view.

Following your moment of zen, head for the rocks to the east. They look dangerous, sure, but they’re safe, so long as you’re careful and mindful of your steps. If you follow the rocks all the way around the lighthouse, not only will you be at the easternmost bit of land in New York State, you’ll also find another beach on the other side. Here, you can find a series of trails that will take you into Camp Hero State Park, where you’ll find, arguably, the most scenic spot in all the Hamptons, the Bluff Lookout.

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