7 Best Hiking Trails On The East End

Here are seven of the best hiking trails the East End offers to keep you active.

1. Linda Gronlund Trail Loop

The Linda Gronlund Trail Loop is a 3-mile hike in Sag Harbor through the Linda Gronlund Memorial Preserve. Also known locally as Barcelona Point, the loop features dune cliffs with vistas of the azure waters of Sag Harbor Bay and the historic Cedar Island Light, a charming lighthouse dating from 1839. One will also find verdant moss beds amid the tree roots along the path to the dunes, a perfect spot for lunch with a view. Dogs are welcome too, as long as they are leashed.

Finding this dazzling trail can prove tricky to first-timers, as it hides behind the Sag Harbor Golf Course. To best access the Linda Gronlund Trail Loop from downtown Sag Harbor, hikers should turn left from the East Hampton-Sag Harbor Turnpike onto Barcelona Neck Road. Barcelona Neck Road merges into Trustees Road once inside the golf course, which you will follow up to the clubhouse. You turn right at the fork in the road and follow the unpaved road toward the trailhead. At the end of Trustees Road, you will find ample space for parking. As the road is unpaved, it can get muddy after rain, so consider hiking boots over sneakers if hiking on a damper day.

2. Battery 113 Trail

Battery 113 Trail, located in Montauk’s Camp Hero State Park, is a 2.1-mile out-and-back trail (meaning once you reach the endpoint, you return the way you came). Striding through the changing leaves with the sound of the nearby waves, Battery 113 makes for a peaceful afternoon hike. However, one might be surprised to learn they are trekking through a place shrouded in conspiracy and pop culture: Camp Hero, once part of the now-defunct Montauk Air Force Station, helped inspire the hit Netflix series Stranger Things (at one point titled Montauk). You can still feel that air of mystery as you look up at the radar tower looming over the park, the last AN/ FPS-35 radar tower still standing in the world. Leashed dogs are also welcome to join in the hiking fun on the Battery 113 Trail.

Battery 113 Trail can be reached by turning left on Old Montauk Highway from Route 27 as you approach the Montauk Lighthouse. From there, you continue until you reach the guard station for Camp Hero State Park. The trailhead is located to the left of the guardhouse. The park’s hours of operation are listed as sunrise to sunset year-round. There is a fee of $8 for vehicle entrance, collected between 8 a.m. and 4 p.m. Hikers can find parking farther down the road in the Camp Hero parking lot, which overlooks the impressive Montauk cliffs.

3. Shadmoor State Preserve Trail

East End visitors seeking a close, convenient outing should look no further than the Shadmoor State Preserve Trail. A 2.5-mile loop trail in Shadmoor State Park is a stone’s throw from downtown Montauk and the famed surf break at Ditch Plains. In terms of natural splendor, Shadmoor has much to offer: sandy dunes; steep, weathered cliffs; and the low, flowering brush local to Montauk foliage. Shadmoor State Preserve Trail is also dog-friendly, allowing them to be unleashed in certain areas.

The Shadmoor State Preserve Trail is only a three-minute drive from the central downtown plaza and a 16-minute commute by foot. Parking for the trail is immediately off Montauk Point State Parkway on the right side of the road. The trailhead, located behind the parking lot, is easily accessible.

4. Big Woods Preserve

Visiting Southampton’s Big Woods Preserve is a great way to practice shinrin-yoku—or the Japanese art of forest bathing. As the seasons change and the maritime beech trees are alight with orange and red hues, forest bathing, typically an outdoor mindfulness practice, becomes a stunning event of its own. Big Woods Preserve is a loop trail with a length of 2.3 miles and boasts some of the most untouched coastal wetlands in Long Island’s East End, home to the endangered piping plover. At one point in the loop, the trail will take you alongside Big Fresh Pond, a large body of freshwater nestled in the woods and stocked with largemouth bass, chain pickerel and yellow perch, among other fish species.

To reach Big Woods Preserve from downtown Southampton, take North Sea Road to where it forks with West Neck Road, then turn left onto West Neck and continue to Millstone Brook Road. Once at Millstone Brook Road, turn left and continue up the road until you reach the trailhead. The trail is marked with a sign announcing it as the Marguerite Crabbe Greef Wildlife Sanctuary, and you can park directly in front of the trailhead.

5. Joan C. Coles Loop

If you want to make a day out of your hiking adventure (or simply get those extra steps in), check out the Joan C. Coles Loop on scenic Shelter Island. Nestled in the 2,350-acre Mashomack Preserve, the trail is a 7.9-mile trek through the tidal creeks, marshes and oak woodlands that comprise Shelter Island’s impressive flora. Due to its large size and secluded nature, the Joan C. Coles Loop is a great place to forget about the bustle of life for a moment and lose yourself in the rustles of tree limbs and the chirp of resident blue jays. Bring a friend or loved one to bask in the natural beauty, but leave your dogs at home for this hike.

Visiting the Mashomack Preserve as a visitor to Shelter Island requires a brief ferry ride. There is a small fee for the journey: The South Ferry from Sag Harbor costs $15 one way and $20 round trip per vehicle, with an additional $2 per person, while foot passengers only need to pay $2 ($3 for same-day return). Once you disembark from the ferry, continue on South Ferry Road until you reach the Mashomack Preserve on the right side. There is parking near the trailhead once you pass through the gates.

6. Cedar Point

Though the changing seasons mean trading bathing suits for snug sweaters, kissing the beach goodbye on the East End is hard. East Hampton’s Cedar Point County Park offers a 3.1-mile loop trail to satisfy that fix for your feet in the sand. The Cedar Point trail circumnavigates the peninsula that lends the path its name, snaking leisurely along the Barcelona Bank and Gardiner’s Bay coasts. Due to its sandy terrain, the low American seagrass allows you to gaze across Cedar Point and enjoy the views on each side. Beach-loving dogs are welcome too, as long as they are leashed. The trail’s midpoint brings you to the Cedar Island Light, a local historical treasure standing since the 1830s.

One must enter Cedar Point County Park from Alewife Brook Road to reach the loop trail. The entrance to the park is on the left side of Alewife Brook Road, heading north, clearly marked by a sign. Once inside the park, continue up Cedar Point Road until you reach the Cedar Point Camp Store & Safari Tent Glamping, with nearby parking. As a hiker in the East End, it is essential to note that pests, such as the Lyme disease-carrying American dog tick, are present in Cedar Point County Park, so check your dog’s fur and body after hiking there.

7. Walking Dunes Trail

Located in Hither Hills State Park between Montauk and Neapauge, Walking Dunes Trail, a loop trail 2.7 miles long, is another Hamptons beach hiking favorite. Hikers will traverse pebbly beaches and grassy dunes, with scenic vistas overlooking Neapauge Harbor and Neapauge Bay waters. Other interesting sights along the trail are an intricately constructed hut made from smoothed driftwood and the remains of a brick chimney, still partially intact. A sign along the trail welcomes you, explaining the 80-foot-tall dunes “walk” (or erode) 3.5 feet each year due to the strong winds shifting the sand.

Walking Dunes Trail is easy to locate: When driving west on Montauk Highway, turn left onto Neapauge Harbor Road by the Hither Hills Racquet Club. Neapauge Harbor Road dead-ends into the trailhead for Walking Dunes Trail. You can park your car along the road before entering.