{"id":27368,"date":"2012-02-20T07:00:33","date_gmt":"2012-02-20T11:00:33","guid":{"rendered":"https:\/\/offmetro.com\/ny\/?p=27368"},"modified":"2025-08-21T10:02:08","modified_gmt":"2025-08-21T14:02:08","slug":"hiking-trails-long-island","status":"publish","type":"post","link":"https:\/\/offmetro.com\/ny\/27368\/hiking-trails-long-island\/","title":{"rendered":"The 10 Best Hiking Trails on Long Island"},"content":{"rendered":"

Earn your hiking stripes and bragging rights by exploring hiking on Long Island’s finest trails. Traverse past haunted lighthouses stuffed with peg legs, otherworldly landscapes, sunbathing seals, and sparkling seasides.<\/p>\n

Don’t let your newfound sense of entitlement on the trails go to your head unless you go boot to boot with Stephen Talkhouse. A native American who died in the 1920’s, Talkhouse was known for unabashedly boasting about walking from Montauk to Brooklyn and back in a single day. We don’t recommend walking the expanse of island in a day, but you can pay your respects to the tall tale hiker by stopping off at Stephen Talkhouse Tavern in Amagansett<\/a>, Long Island (or one of our other favorite breweries)<\/a> for some cold brews and live music after a long, fortifying day on the trails.<\/p>\n

Here are our picks for the 10 best hiking trails on Long Island (with a map at the end!)<\/strong><\/p>\n

David Weld Sanctuary | Nissequogue<\/strong><\/h2>\n

Richard \u201cBull\u201d Smythe won the land that is now called the David Weld Sanctuary when he bet a Native American Chief he could ride a bull around from sunrise to sunset. Smythe and his pet bull, Whisper, won the completely worthwhile bet and laid claim to the deciduous forest.<\/p>\n

Today you can hike along towering tulip trees, gurgling swamps, red cedars, and glacial erratics. Stop at the bluff along the Long Island Sound and carefully venture downhill onto the beach for a hike along the shoreline.<\/p>\n

How to get there:<\/strong> Take the LIRR out of Penn Station to the Kings Park stop. Once you arrive, catch a cab to David Weld Sanctuary and tell the driver it’s off Horse Race Lane and the T with Boney Lane. Download the trail map: David Weld Preserve.<\/a>
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\nMashomack Preserve | Shelter Island<\/strong><\/h2>\n

The \u201cJewel of the Peconic\u201d stretches across nearly one-third of Shelter Island<\/a> (not be confused with Leonardo DiCaprio’s Shutter Island.) You’ll have your pick of dense trails from short and sweet to an all day hike past 10 miles of coastline, salt marshes, foot bridges, and wildlife. You might even spot an endangered piping plover. Hiking Mashomack is akin to finding a wooded paradise in the middle of small town living.<\/p>\n

How to get there:<\/strong> Take a train out of Penn Station to Greenport and walk to the North Ferry station. Take the ferry to Shelter Island and either call a cab or ride your bike approximately five miles to Mashomack Preserve.<\/em><\/p>\n

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