LOCALS’ TOP 5 MUST-VISIT SPOTS ON SHELTER ISLAND
We asked our residents where they take their friends when they come to visit Shelter Island. Here’s what the locals say are the places not to miss.
1. Mashomack Preserve
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Known as the "Jewel of the Peconic," this 2,350-acre nature preserve is a wonderland for wildlife enthusiasts and hikers alike. The preserve offers four well-marked trails varying in length from 1.5 to 11 miles, allowing visitors to immerse themselves in tidal creeks, woodlands, and fresh marshes. Local tip: keep an eye out for ospreys, as Mashomack Preserve is one of the largest havens for them in New York. You can download a map of the preserve on the Nature Conservancy’s website.
2. Sylvester Manor Educational Farm
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Take a step back in time at Sylvester Manor Educational Farm. Established in 1652, this historic plantation and now a working organic farm offers a unique experience to visitors. Locals suggest touring the Manor house, exploring the expansive grounds, and making sure you don’t forget to stock up on fresh, farm-grown produce or a jar of homemade jam from the farm stand. You’ll also find the Devil’s Footprint that we wrote about in our free guide to the little-known historic places on Shelter Island. Sylvester Manor is a tangible connection to Shelter Island's colonial history and an inspiration for sustainable living.
3. Crescent Beach
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This gorgeous stretch of sandy beach on the island's west side offers visitors a perfect spot for swimming, sunbathing, or simply enjoying the beautiful views of the Peconic Bay. The sunsets here are truly spectacular. In the summer, you might also want to visit the Sunset Beach Restaurant and Bar beachfront restaurant right across the street, which turns into a lively spot in the evenings. During the summer season, there are lifeguards on duty and restrooms on-site. You can learn more about this beach and others, as well any permits required, on our Shelter Island Beaches page.
4. Shelter Island Historical Society
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If you're a history buff, the Shelter Island Historical Society is a must-visit. Housed in the 1743 Havens House, this center provides a fascinating insight into the island's history. Peruse artifacts, photographs, documents, and a wealth of information about the island's past. The historical society also hosts a variety of events throughout the year, including their famous annual Black and White Benefit.
5. Shell Beach
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Shelter Island locals often direct visitors in search of peace and quiet to Shell Beach. This hidden spot, located off a narrow and unmarked dirt road, is known for its shells – hence the name – and serene atmosphere. It's a perfect place for a secluded picnic, kayak excursion, or a day spent exploring the sea's edge for marine life. Remember to respect the beach's tranquility and leave it as clean (or cleaner) than you found it. Please note there are no facilities or lifeguards at this beach. You can learn more about this beach and others, as well as any permits required, on our Shelter Island Beaches page.
Dining and Shopping
No doubt, all this activity will work up your appetite. Fortunately, we have a great Shelter Island restaurant guide. And there are great places to shop, too.
These local recommendations offer just a taste of what the island has to offer. Whether you're a nature lover, history enthusiast, or beachgoer, Shelter Island awaits with open arms and untold stories.