Five Must-See Hiking Trails in the Hamptons and Beyond

Closeup of male legs hiking in nature.
Photo: iStock

Looking to add some hiking to your list of activities this fall? Never mind the fact that Long Island’s elevation barely breaches 400 feet above sea level (in one spot), there are still plenty of hidden treasures worth seeking out if you want to savor everything the Island has to offer. The beach will still be waiting for you once you hang up your boots for the day. Take an afternoon to explore the other areas that make this island of ours feel so vast and rich with adventure.

1. Long Island Pine Barrens (Manorville). The Pine Barrens feature perhaps the most extensive set of walking paths, ponds and scenic diversions that the Island has to offer. A day can be spent wandering through lightly sanded trails beneath gargantuan trees, and there will still be plenty left over to discover. This jaunt will take you through the Rocky Point Preserve, the Peconic River Watershed and the small treasure of Sears Bellows County Park in Hampton Bays. Don’t set out to cover everything all at once; these trails are best appreciated when taken in one piece at a time.

2. Long Island Greenbelt Trail (East Islip, Sunken Meadow). Completing the Greenbelt Trail is a mark of honor for any Long Island hiking enthusiast. It spans 32 miles and connects the Island’s north and south shores, so expect the hike to take a full day, assuming you stop to take in the scenery now and again. Hikers have the option of beginning on the North Shore at Sunken Meadow State Park or on the South Shore at Heckscher State Park, and either option can guarantee a great beginning and ending to a long, fulfilling day on the trail.

3. Red Creek Town Park (Southampton). The Red Creek Park is highly suitable for hikers who seek a less grueling day on their feet while still availing themselves of the beauties the Island has to offer. In close proximity to the hustle and bustle of the  Hamptons, the five-mile Red Creek trail weaves through enough interesting terrain flush with magnificent flora and fauna to give hikers a satisfying peace of mind without feeling too exhausted to enjoy the rest of the spent back in civilization.

4. Seal Haulout Hike/Money Pond Trail (Montauk). The Haulout Hike trail, which kicks off at the Island’s easternmost point, is one not to be missed—watch for seals. Take your time exploring the rocky shores of one of the Island’s proudest places and let the cool smell of the ocean’s mist remind you of what makes living in a seaside town so rewarding. Expand your trip along the Money Pond Trail and you’ll wind through more hidden relics of what feels like a piece of the world immune to the impact of changing times.

5. Elizabeth A. Morton Wildlife Preserve (Noyac). If you’re making your way to Sag Harbor from Southampton along Noyac Road, be sure to put aside an hour or so to explore this incredible wildlife preserve. The area features an accessible walk through shady wooded areas before opening up to an incredible beach primed for fans of sunsets. Before visiting, be sure to pick up a bag of birdseed (or sunflower seeds) for the hungry chickadees waiting in the trees. Just hold out a hand and watch as these trusting birds land in your palm to accept your gifts. It reminds us of how we big, sophisticated creatures can still rely on the little guys to surprise us now and again.

As always, it’s important to come prepared when setting out for a day on the trails. Bring more water than you think you’ll actually need and some nuts or granola to refuel your engines as you press on towards the next awesome moment. When your day is done, check yourself, your family and your pets for ticks before settling in for bed. Tall grass and marshes are a hotbed for those little buggers, but that shouldn’t stop you from basking in all the splendor the Island has to give.

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