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Explore the East End: 5 Must-Try Hiking Trails to Embrace Autumn's Beauty

As the autumn season settles, even if the beach starts to get a bit too breezy, there are plenty of ways to take advantage of the incredible East End outdoors. Here are our five favorite hiking trails to help you burn off all that Halloween candy and pumpkin pie.


Barcelona Point, Sag Harbor

Just a mile outside of Sag Harbor Village, this 3-mile hike through the Linda Gronlund Memorial Preserve to Barcelona Point (pictured in header) offers a scenic loop of dune cliffs with breathtaking views of Sag Harbor Bay and the historic Cedar Island Lighthouse. Verdant moss beds line the path to the dunes, providing an ideal spot for a picturesque lunch, and with dogs allowed on leashes it’s the perfect adventure to bring our furry friends. The start of this trail is easily accessible, located behind the Sag Harbor Golf Course off of 114.


Cedar Island Lighthouse.

Cedar Point, East Hampton

Embrace a 3.1-mile loop trail at East Hampton's Cedar Point County Park, where leashed dogs are welcome. This sandy trail offers beautiful views across to both Barcelona Point and Gardiner’s Bay coasts, and you'll also find the historic Cedar Island Lighthouse at the midpoint. Enter Cedar Point County Park from Alewife Brook Road to access the loop trail.


Walking Dunes Trail, Montauk

Located in Hither Hills State Park, the 2.7-mile Walking Dunes Trail is a favorite among Hamptons beach hikers. This trail offers pebbly beaches, grassy dunes, and scenic vistas of Napeague Harbor and Bay waters. Notable sights include an intricately constructed driftwood hut and the remains of a brick chimney. The trail is well-marked and easily accessible by turning onto Napeague Harbor Road from Montauk Highway.


Big Woods Preserve, Southampton

Big Woods Preserve in Southampton is perfect for practicing "shinrin-yoku," the Japanese art of forest bathing, especially as maritime beech trees change color. This 2.3-mile loop trail showcases some of the most pristine coastal wetlands in Long Island's East End and is home to the endangered piping plover. Accessible via North Sea Road and Millstone Brook Road, the trailhead is marked as the Marguerite Crabbe Greef Wildlife Sanctuary.


Joan C. Coles Loop.

Joan C. Coles Loop, Shelter Island

The 7.9-mile Joan C. Coles Loop on Shelter Island offers a day of hiking through tidal creeks, marshes, and oak woodlands in the 2,350-acre Mashomack Preserve. It's an excellent place to disconnect from the hustle and bustle of life, although it's unfortunately not dog-friendly, it’s still well worth the visit. Reach the Mashomack Preserve via a short ferry ride from Sag Harbor.


Of course, we will always love to bundle up to brave the beach, especially for sunrises and sunsets, these East End hiking trails also provide the perfect vantage point to watch the seasons change with the colors. Just make sure to wear long socks, pants, and always check for ticks! If you have any questions about East End hiking or what else makes it a great place to call home, get in touch with us!

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