Know the New Hiking How-tos
Rockwood Hall at Sleepy Hollow
Directions to trailhead
Take the New York State Thruway to Exit 9 (on the east side of the Tappan Zee Bridge). Turn right at the top of the ramp onto US 9 (South Broadway), and continue north on US 9 through the Village of Tarrytown. After 1.7 miles, you’ll come to a complex intersection where you should bear left to continue on US 9. In another 1.8 miles (3.5 miles from the Thruway exit), immediately after crossing under NY 117, turn right at a sign for “Rockwood Road,” and follow the ramp onto NY 117. After reaching a stop sign, continue ahead through an intersection, following the sign to “Kendal on Hudson,” pass an exit from a parking area on the left, then turn left at the entrance to the parking area.
Rockwood Hall is the site of the former summer home of William Rockefeller (1841-1922), brother of John D. Rockefeller. In 1886, he purchased Rockwood, a 200-acre estate, and built Rockwood Hall, a mansion with 204 rooms. Frederick Law Olmsted designed the landscape, which includes many ornamental trees. Following Rockefeller’s death in 1922, the estate was converted into a country club, which soon went bankrupt. In 1937, the property was acquired by John D. Rockefeller, Jr., William’s nephew, who arranged for the mansion to be razed in 1941-42.
The Rockefeller family donated Rockwood Hall to New York State in 1999, and it now forms a part of Rockefeller State Park Preserve. Although the buildings are gone, the foundations remain, and the carriage roads that were constructed by the Rockefeller family offer an opportunity for a delightful stroll through the property, with panoramic views over the Hudson River. Bicycles are not allowed, although equestrians are permitted (with a permit). Although not blazed, the roads followed by this hike are easily followed.
From the western end of the parking area, follow the crosswalk across the paved entrance road, bear right onto a wide paved road (closed to traffic) and continue uphill on a narrower road. At a kiosk at the top of the climb, bear right onto another road, surfaced with paving stones, soon reaching a spectacular viewpoint over the Hudson River.
After passing a huge weeping beech tree, a path diverges to the right, but continue ahead, passing stone foundation walls to the right. These walls are all that remains of William Rockefeller’s huge mansion. As you approach the highest point along the road, the views of the Hudson River broaden, and you can see the Tappan Zee Bridge to the left, beyond the Kendal on Hudson retirement community.
You may hear the sound of trains directly below you. Metro-North’s Hudson Line runs along the east shore of the river, and you can clearly hear (but not see) the passing trains (you’ll be able to see them later on in the hike).
After taking in the view, continue ahead along the road, which descends in a sweeping curve, bordered by stone walls. At the next intersection, turn left. Almost immediately, you’ll reach a Y-intersection. Here, you should take the right fork, following the sign for the “Upper Trail.” You’re now proceeding along a paving-stone road that climbs very gently, soon passing a grassy field on the right.
The road crosses another wooded area and descends to an open expanse, with grassy areas on both sides. Continue along the road, which passes a viewpoint over the Hudson River at the end of the grassy area, curves sharply to the right and reenters the woods.
Before reaching the end of the gravel road at a locked gate, turn left at a blue signpost for the Brook Trail and follow this trail downhill, bearing left at the fork. At the base of the descent, turn left onto a gravel road which proceeds through a ravine studded with rhododendron, crossing four bridges over the brook in close succession. Continue to follow the road, which parallels the brook, until you approach the shore of the Hudson River (at a sign for the “Lower Trail”).
Just ahead, you’ll come to a viewpoint over the river. To the right (north), you can see Croton Point jutting out into the river in the distance. The railroad tracks are visible below, and you may see a Metro-North or Amtrak train zoom by. Continue along the gravel road, which now heads south, with a grassy slope on the left and the river on the right. Breaks in the dense vegetation afford views over the river, and benches have been placed along the trail, inviting you to pause and take in the views.
After passing a huge oak tree on the left, you’ll come to a fork. Here, you should bear right (following the sign for the “Lower Trail”) and continue heading south along the river. Soon, you’ll see stone walls above a grassy slope on the left. These walls mark the site of the Rockefeller mansion that you passed by earlier on the hike.
At the southern end of the Rockwood Hall property (marked by a number of evergreen trees), there are panoramic views up and down the Hudson River. A bench has been placed here, and you may wish to pause once more to enjoy the views.
Continue along the gravel road, which bears left and begins to head east. At the next intersection, a path to the right leads into the Kendal on Hudson property, but you should continue ahead on the gravel road, which winds uphill. Upon reaching another path which heads into Kendal on Hudson, bear left and continue uphill on the gravel road, now bordered on the right by boulders and a stone wall. When you reach the kiosk, bear right and head down to the parking area where the hike began.
To view a photo collection for this hike, click here.