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.
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, Long Island for some cold brews and live music after a long, fortifying day on the trails.
Here are our picks for the 5 best hiking trails on Long Island:
David Weld Sanctuary | Nissequogue
Richard “Bull” 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.
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.
How to get there: 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.
Mashomack Preserve | Shelter Island
The “Jewel of the Peconic” stretches across nearly one-third of Shelter Island (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'll also be able to see lots of reptiles, such as lizards, turtles and snakes. Long Island has 13 different species of native snakes. However, none of these are venomous or poisonous snakes so no worries. Hiking Mashomack is akin to finding a wooded paradise in the middle of small town living.
How to get there: 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.
Sunken Forest | Fire Island
Leave the hysteria of Fire Island party hopping behind and head out to the Sunken Forest. The rare Maritime Holly Forest hosts trails nestled into the side of a dune surrounded in some 300 year old American Holly trees. You’ll also brush up against a canopy of sassafras, black oak, and shadbush among other beauties. Avoid trying to hang from the mysterious vines tangling through the forest lest risk damaging the habitat – and stumbling into briars and patches of poison ivy.
How to get there: Take Long Island Railroad’s trains out of Penn Station to the last stop in Sayville then catch a commuter van to the ferry. The Sayville Ferry runs to Sailors Haven on Fire Island throughout the season.
Caumsett State Park | Lloyd Harbor
Check out the grounds of the heir to a department store fortune, Marshall Field III, at Caumsett State Park. His Winter Cottage nestled on the 1,750 acre land is easily the size of a small mansion and makes your fab vacation spot upstate look like a lean-to shanty. Hike along the paved trails or venture off into more wooded territory for bird-watching, fishing, nature study, horseback riding, salt marshes, and a dairy complex.
How to get there: Take the LIRR out of Penn Station to the Huntington stop. Caumsett State Park is a 15-minute cab ride.
Walking Dunes of Hither Hills State Park | East Hampton
Venture into the mystique of the Walking Dunes of Hither Hills State Park and resist the impulse to hunt for attacking Tusken Raiders circa Star Wars. These parabolic dune fields constantly shift southeast uncovering a forgotten forest. Red-tailed hawks and osprey can be spotted flittering past beach plum and bayberry. Notice the markers dotting the short hike through the dunes and stop at number 8 revealing the Phantom Forest that once thrived with vegetation. Now you’ll find a collection of ominous stumps uncovered in the wake of the walking dunes.
How to get there: Take a train out of Penn Station to the East Hampton stop. Or catch a ride on the Hampton Jitney to East Hampton. Catch a 15-minute cab and tell the driver Route 27 to Napeague Harbor Road at Hither Hills State Park.
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