Round Pond Trail, Photographed by Kimberly A. Kakerbeck
By Alexander Powers, BHS Content Team
As the seasons transition from vibrant autumn hues to the stark beauty of early winter, the Hamptons offers some of the most breathtaking trails to explore. Whether you're looking for a peaceful walk surrounded by foliage or a more challenging hike with rewarding vistas, these trails are perfect for immersing yourself in the natural splendor of the East End. Here's a curated list of the best hiking trails, with expert recommendations from Brown Harris Stevens real estate agents.
Round Pond Trail
“I love Round Pond Trail, which is part of the Long Pond Greenbelt. Living at the end of Round Pond Lane allows me to step out of my door and onto the trail, which winds around several stunning ponds.” - Kimberly A. Kakerbeck
Quogue Wildlife Refuge
“One of my favorite places to hike is the Quogue Wildlife Refuge. The paths wind along the edge of the Old Ice Pond, with fall colors reflecting beautifully off the water. Depending on your desired distance, the four paths range from 0.8 miles to 3.1 miles. You can also visit various animals that either live at the refuge or are temporarily being rehabilitated.” - Lauren A. Battista
Hither Hills State Park
“Hither Hills offers a variety of hiking options with local vegetation transitioning beautifully into fall and winter. If you’re lucky, you might even spot some beach plums along the way!” - J.B. DosSantos
Trout Pond Park
“Trout Pond Park, located off Noyac Road and Ruggs Path in Sag Harbor, is a hidden gem. The serene combination of water, hiking trails, and the vibrant seasonal colors makes this park a perfect destination." - Cynthia Barrett
Mashmack Preserve
"Mashomack Preserve on Shelter Island offers trails for all ages and experience levels. Spanning over 2,350 acres, this preserve features tidal creeks, woodlands, and freshwater marshes, all preserved by The Nature Conservancy and local residents.” - Cynthia Barrett
The Kurt Billings Loop
“The Kurt Billings Loop offers stunning views, including a peek at Connecticut on a clear day. The trailhead is on West Neck Road. For a dramatic experience, the trail from Hither Hills to the Montauk Lighthouse is breathtaking, especially when wild tidal surges crash below, providing a natural lesson in erosion. - Hailey McGowin
