Linda Gronlund Trail Loop
Tucked away in Sag Harbor, the Linda Gronlund Trail Loop—known locally as Barcelona Point—is a scenic 3-mile hike through the Linda Gronlund Memorial Preserve. The trail winds through mossy forest floors and under a leafy canopy before opening onto dune cliffs with sweeping views of Sag Harbor Bay and the historic Cedar Island Light, a lighthouse dating back to 1839. It’s the kind of spot that invites a pause—maybe for a picnic, maybe just to breathe it all in. Leashed dogs are welcome too.
Battery 113 Trail
Winding 2.1 miles through Montauk’s Camp Hero State Park, the Battery 113 Trail offers a serene, out-and-back hike where the rustle of leaves meets the distant crash of ocean waves. But beneath its peaceful exterior lies a story laced with intrigue—this former military base, once part of the Montauk Air Force Station, is steeped in conspiracy lore and even inspired Stranger Things (originally titled Montauk). Leashed dogs are welcome on the trail, adding to the charm of this quietly cinematic coastal escape.
Shadmoor State Preserve Trail
Just minutes from downtown Montauk and the legendary Ditch Plains surf break, the 2.5-mile Shadmoor State Preserve Trail offers an easy, scenic escape into Montauk’s untamed beauty. The loop winds through sandy dunes; steep, weathered cliffs; and stretches of native flowering brush that define the East End landscape. Close enough for a quick outing yet rich in natural drama, it’s a favorite of locals and visitors alike. Best of all, it’s dog-friendly, with some areas where pups can explore off leash.
Big Woods Preserve
The 2.3-mile loop at Big Woods Preserve winds through pristine coastal wetlands, home to the endangered piping plover. Midway, hikers reach Big Fresh Pond—a hidden freshwater lake teeming with bass, pickerel and perch.
Joan C. Coles Loop
For a longer, more immersive hike, head to the Joan C. Coles Loop on Shelter Island. Tucked within the 2,350-acre Mashomack Preserve, this 7.9-mile trail winds through tidal creeks, marshes and oak woodlands, offering a peaceful escape into nature’s rhythm. It’s a perfect spot to unplug and soak in the sounds of rustling trees and calling blue jays.
Cedar Point
Cedar Point County Park in East Hampton features a breezy 3.1-mile loop that hugs the coastline of Barcelona Bank and Gardiner’s Bay. With sandy paths and low seagrass, the trail offers sweeping views in every direction, plus a chance to spot the historic Cedar Island Light at the halfway point. Leashed, beach-loving dogs are welcome too.
Walking Dunes Trail
Tucked in Hither Hills State Park between Montauk and Napeague, the 2.7-mile Walking Dunes Trail is a local favorite for coastal hikes. The loop winds through pebbly beaches and grassy dunes, with sweeping views of Napeague Harbor and Bay. Along the way, you’ll spot a driftwood hut, the remains of a brick chimney and a sign explaining how the 80-foot dunes “walk” nearly 4 feet each year, carried by the wind.
