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USA/Mid-Atlantic: Pocantico Hills and Sleepy Hollow, NY

The Home of Ichabod Crane

A Recommended Walk


Time: 1 1/2 hours to 2 1/2 hours

Distance: Up to 3 1/2 miles

Parking: There's ample parking near the park entrance.

Highlights: An idyllic setting of meadows, forests, hills, and a bubbling river in a shaded forest. Bridle paths make for easy walking, with enough ups and downs to get a good workout. Serious hikers: Don’t be put off by the bridle trails and signposts. This park has a magical combination of scenery, history, and legend.

Viewpoints: The beauty of this park comes from the combination of forest, meadow, bridle paths, and sense of history. The best views do not stretch for miles, yet reveal pastoral scenes suggestive of the English countryside. There is a particularly nice view, however, from Eagle Cliff (not really a cliff). For the best views in the area, get back in your car and drive to Rockwood Hall (see Recommended Walk 2).

Precautions: The walk follows well-groomed bridle trails, so it’s almost impossible to get into trouble unless the weather is bad.

Trail blazes: Rockefeller State Park has a trail blaze system and signposts with trail names.

Maps: The park’s visitors center has maps. Some of this walk covers an area that is open to the public but not officially part of the park, so the maps may not cover the entire walk.

To Begin:

Old Sleepy Hollow Road Trail

From the parking lot, proceed southwest away from the visitors center toward a gravel road heading into the forest. The highway is off to your right. You are now on Old Sleepy Hollow Road, one of the oldest roads in the area, dating back to at least colonial times. It likely was originally a Native American trail. The trail proceeds steadily downhill.

Waypoint 1

Cross Sleepy Hollow Road. There’s a sheltered sign with park information. Proceed straight down the bridle path.

Waypoint 2

Shortly after crossing the Pocantico River, go left on a bridle trail. This is the Pocantico River Trail, which you will follow on your way back. It is marked by small signs at major intersections.

Waypoint 3

Make a right uphill. This is Eagle Hill Trail. Follow it uphill for about 10 minutes.

Waypoint 4

View from Eagle Hill Summit

At the top of the hill, a trail leads to the left. A signpost points to Eagle Hill Summit. As you proceed uphill, you will see a bridle path join the trail from your right. Your loop will take you back to this spot a short while later.

Proceed straight to a viewpoint, where there is a fine view south of the meadows, forests, hills, and the Hudson River. To the left, on a hilltop, you may spot a glimpse of Kykuit, the home of the Rockefellers, which is open to the public for tours by reservation. From the viewpoint, proceed on the loop until it rejoins the bridle path you followed on the way up. Go left and retrace your steps to Waypoint 3. Go left and follow the trail as it winds its way downhill. (Or, to shorten the walk, you can go right and retrace your steps to your car.)

Waypoint 5

Alongside Old Gory Brook Rd.

The trail reaches a T intersection. Go left onto another bridle path. This is Old Gory Brook Road, another of the park’s ancient roads. It was named for a particularly bloody battle between two Native American tribes.

On the hillside to your right, barely visible when leaves are on the trees, is Spook Rock. While the Native American ghost story is haunting, it's no more than a large rock in the forest and not worth the detour unless you want to extend the walk and have a park trail map.

Continue along Old Gory Brook Road until you reach an intersection. Bear right and cross a bridge over the Pocantico River.

Waypoint 6

After crossing the Pocantico River, make a right. This is the Pocantico River Trail. Go a short distance. Pass an unused concrete bridge on your right. Continue toward another bridge. Before you reach it, turn left. This is a continuation of the Pocantico River Trail. If you feel sleepy in this part of the walk, it might be because of a spell placed on this spot by a Native American wizard to put an enemy tribe to sleep; hence the name, Sleepy Hollow.

Follow the river for a short distance along the valley floor. You will soon see the towering wall of the Croton Aqueduct as it looms over the valley floor.

Waypoint 7

Stone bridge by Croton Aqueduct

With the aqueduct towering in front of you, and an old stone bridge to your right, bear left up a hill. The aqueduct will be to your right. Admire the stonework built by manual laborers in the 1830s to feed New York City's growing thirst for water.

Waypoint 8

You soon reach an intersection with a bridle path that's on your left. Turn left and follow the bridle path as it winds gently uphill with a meadow to your left and a view of Eagle Cliff in the distance. The path levels off and then descends gradually toward another field. Ignore a trail on your right and continue downhill.

Waypoint 9

You reach a T intersection. Go left onto another bridle path. To your left is a forest; to the right, a beautiful meadow with forested hills beyond. The trail gradually descends into the Pocantico River Valley.

Waypoint 10

Make a right. This is the Pocantico River Trail. The river will be on your left as you proceed a short distance.

Waypoint 11

View near Waypoint 11

Make a left onto a stone bridge over the Pocantico River. Bear right on to the bridle path — the Pocantico River Trail. The river will be to your right as you proceed back toward your car. It takes about 10 minutes to return to Waypoint 3, where you retrace your steps to your car.

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