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USA/Mid-Atlantic: Montauk, NY

Cowboys & Tribes, Poachers & Spies

A Recommended Walk


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Time: 2 or 3 1/2 hours
Distance: 3 or 6 miles

At the back corner of the overview parking lot, next to a sign for Petticoat Hill Trail, Elisha's Valley Trail and Fresh Pond, walk to the left behind a guard rail, following a black arrow. In 20 or 25 steps, you arrive at the back of an overview information sign. Turn right and follow a path as it leads downhill through scrub pines and into a forest. Ignore a small trail to the right and continue through the woods until you emerge onto a 6-foot-wide sandy road.

Waypoint 1

Waypoint 1Turn right onto the road. Ignore a dirt path to the left.

Waypoint 2

At a junction of two dirt roads, follow the narrower dirt road on the right. Proceed through the woods uphill.

Waypoint 3

At a junction of two dirt roads, turn left. When you reach a wide paved road, cross it and continue on a sandy road to a stop sign and railroad tracks. Beware of Long Island Railroad trains. Make sure to look in both directions before crossing. Cross the railroad tracks.

Waypoint 4

Napeague Bay from Waypoint 5At a junction several yards ahead, follow a sandy road that veers to the right. Ignore a road to the left leading to a pond and a narrow trail on your extreme right that goes through the woods to Native American ruins. Further along, ignore another dirt road to your right and continue straight. You emerge from the woods near the shoreline of Napeague Bay. Proceed to the beach. The beach, with its tall dunes to the east, makes a scenic picnic spot. Swimming, however, is prohibited. With your back to the water, retrace your steps several yards.

Waypoint 5

Turn left, proceeding uphill on sandy Aterfence Trail.

Waypoint 6

Waypoint 6 & Napeague BayAt the top of the hill, go through a gap in a split rail fence and walk straight along a road, proceeding away from the bay. Take a last glimpse at the great bay views. At the next junction, turn left onto the sandy road (the same road you walked on earlier that leads to the bay). At the next junction (Waypoint 4) before the railroad tracks, turn right and head through the trees on a dirt road. Continue to the shoreline of Fresh Pond. You can use the small clearing just before the pond as a relaxing picnic spot. With your back to the pond, retrace your steps and proceed several yards, ignoring a rocky dirt road to the left.

Waypoint 7

Fresh Pond from Waypoint 7Opposite a small parking area for boaters, turn right into the woods, following a trail marked by a white blaze. Pass large rocks at the trail head and go up a small hill. Follow the trail as it turns to the right and winds briefly toward, but eventually away from, the pond. Ignore the next trail on your left and continue straight downhill through the trees, following white blazes. Follow the trail is it turns to the right just before a hill that ascends to the railroad tracks. Continue on, walking parallel to the railroad tracks on your left.

Waypoint 8

At a trail junction marked by a white right-turn blaze (see optional extension below if you'd like to add a few extra miles to the walk), turn left and cross the railroad tracks. Beware of trains.

Waypoint 9

At a paved road (Old Tar Road, also called Highway to Napeague), turn right. Proceed about 10 yards.

Waypoint 10

Turn left and proceed uphill on a wide trail. A small pine forest is on your left. On the trail, notice several nesting boxes designed to lure the eastern bluebird back to its natural habitat.

Waypoint 11

The Atlantic Ocean from Hither Hills West OverviewAt the next junction, walk between two boulders and turn right. Follow the sandy road (you're now walking between Waypoints 1 and 2). Proceed about 30 yards and turn left a few steps past the brown Hither Hills sign. (You're at Waypoint 1.) Retrace your steps to the parking lot.

Optional Extension

Follow the above walk to Waypoint 8. At Waypoint 8, ignore the trail on your left heading over the railroad tracks and turn right onto a dirt trail, following the white blazes. Ignore a path to the right and stay on the white-blazed trail as it winds to the left. After a few minutes, you reach another trail junction.

Waypoint 1A

At the junction, ignore the trail to your left, blocked by a fallen log. Turn right, following an arrow pointing the way to Napeague Harbor and continue on the white-blazed trail as it winds through the woods. You eventually walk next to tree-covered walking dunes on your right. Some of the dunes in this area are migrating to the southeast. At 50 feet in height, they are the tallest dunes on Long Island. Follow the path uphill atop the dunes and continue on as it winds through the woods. Continue on following white blazes for another 15 or 20 minutes.

Waypoint 2A

When you emerge from the woods at paved Napeague Harbor Road, turn left. Look both ways as you carefully cross the railroad tracks.

Waypoint Route

At a stop sign before Montauk Highway (Route 27), turn left and walk on grass alongside the highway (across the street is the Driftwood resort). Beware of vehicular traffic. Pass a restaurant on your left and then a sign (across the street) for Hither Hills State Park.

Waypoint 4A

About 25 yards before a green sign for Montauk and Old Montauk Highway, turn left onto a gravel road (Old Tar Road). Ignore a small road to the left at Hither Hills State Park information signs. Bear right, following the larger road uphill. Continue on with the railroad tracks to your left. Turn right onto a dirt trail (Waypoint 10). (The dirt trail is 10 yards before another road that heads off to the left across railroad tracks.) Continue on uphill and follow the directions in Waypoints 10 and 11 back to your car in the parking lot.

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