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There was a time when the phrase “get lost” was an insult. These days, it’s therapy.

When the world becomes too much for you, Shelter Island — the pearl in the prongs of the North and South forks — has thousands of acres of wooded trails, quiet country roads, and deserted beaches where you can treat your short fuse with a long walk.

Thanks to the work of local organizers and volunteers, a few extremely generous landowners and politicians who established and supported the Community Preservation Fund real estate transfer tax, more than a third of Shelter Island is now open space set aside for the quiet enjoyment of the public. The following are some of the places islanders most love to visit when it’s time to unplug and wander off.


With its well-developed system of trails and miles of pristine woods and creeks, Mashomack Preserve is the closest thing to wilderness on Shelter Island. Cindy Belt, an outreach coordinator at the site, loves to hike the Green Trail.

“You really feel as though you did something when you’ve finished — it has hills,” she said. “Also woods and meadows, and you get some great water views.”

An additional incentive at roughly the halfway point is the newly renovated Manor House, which features a hikers’ bathroom.

On Shelter Island, it’s possible to be all by yourself at the beach. When she wants to be alone, Alison Bavaro — whose hectic summers are spent running the restaurants SALT and PORT with her husband, Keith — heads for the windswept beauty of a strip of beach at the end of Bootleggers Alley.

“You can sit there in the middle of August on a Tuesday and still have it all to yourself,” she said.


A popular beach walk for those who like their solitude invigorated with some exercise can be found in the route from Hay Beach to Ram Island. Start from the Menhaden Lane parking lot (a Shelter Island Town Beach sticker is required) and then walk southeast amid 42 acres of low beach scrub on a short trail, where you’ll pass native grasses and prickly pear cacti.

If that’s enough solitude, you can turn back. Better yet, however, continue along the pebbly beach traveling southeast (the water will be on your left) until you reach a parking area and country road that leads up and over the hill of Little Ram Island and continues to the causeway between Little Ram and Big Ram Island, featuring sweeping views of Gardiners Bay and the Atlantic Ocean on the left. The road climbs again as you reach Big Ram Island and pass the Ram’s Head Inn. Following Ram Island Drive and Tuttle Drive in a loop around Ram Island adds about two miles to the round trip from Menhaden Lane and comprises a total of about eight miles.


Sylvester Manor, with its 225 acres of gardens, farm fields and wooded trails, is a 17th-century farm intimately connected to the history of the island. It’s also another favorite spot for people who just want to get away from it all.

“This is an old land; you feel it when you walk it, that sense of history … of many lives spent here and their relationship to the land that has endured,” archivist Donnamarie Barnes said.

The paths located behind the property’s Manor House lead to a burial site believed to hold the remains of more than 200 people who may have been slaves or indentured servants. Another short trail leads to farm fields and the marshy edge of Gardiners Creek. The area near the creek is thought to have been the site of Native American camps dating back many centuries, before Europeans colonized the area. It’s not unusual to encounter deer or even bald eagles on the trails in this area.


Joe Denny, an avid walker and local organizer of the Shelter Island Trails group, said his favorite place to get lost on the island is the one-mile loop in Sachem’s Woods. The 24-acre site, located in the middle of the island, is accessible on foot from North Midway Road near the intersection with Bowditch Road. Keep in mind that Sachem’s Woods doesn’t have bathrooms, garbage cans or parking and that everything taken there must also be taken out. Denny is leading an effort to establish trails this summer to connect Sachem’s Woods, Sylvester Manor and 30 acres of the Mildred Hird Preserve, creating a significant trail system through open land in the heart of the island.


Getting lost involves getting away, and nothing is more satisfying than paddling away under your own steam. Like a nature walk on water, the Coecles Harbor Marine Trail is a five-mile round trip that parallels a shoreline of salt marsh, fiddler crabs and osprey nests, with a loop around Taylor’s Island, a tiny tombolo with a rustic cabin and a porch perfect for a picnic. The round trip can take up to four hours, not including your picnic. Paddle southeast from the Burns Road boat launch with the shore on your right, following the Marine Trail interpretive map that is available online.

• A map of publicly owned open space on Shelter Island, including all of the places described here, can be downloaded at

• Mashomack Preserve, 17 South Ferry Road, Shelter Island:

• A Sylvester Manor trail map can be downloaded at

• To schedule kayak rentals at Shelter Island Kayak Tours, call (631) 749-1990

• A Coecles Harbor Marine Water Trail map can be downloaded at

This story was originally published in the March 2017 edition of northforker magazine