Schunemunk Mountain via Jessup/Barton Swamp/Dark Hollow Trails Loop

From the parking area, cross the road and proceed south on the joint Jessup (yellow), Sweet Clover (white) and Highlands (teal diamond) Trails, which climb gently to the crest of a field and then descend to a woods road. To the right, you can see Schunemunk Mountain, which you’ll soon climb.

Turn right on the woods road, going past a chain that blocks off the road. When the white-blazed Sweet Clover Trail leaves to the left, continue ahead, now following the yellow blazes of the Jessup Trail. (You’re also following the Highlands Trail, but the teal-diamond Highlands Trail blazes appear mainly at intersections.) The Jessup Trail crosses a field diagonally to the right, re-enters the woods, and soon climbs to a woods road, where it turns right.

Follow the yellow blazes along the woods road for about half a mile. Watch for a sharp left turn, where the trail leaves the road and climbs to cross the railroad tracks. This is an active rail line, so be sure to stop, look and listen for approaching trains before crossing.

On the other side of the tracks, the Jessup Trail turns right, briefly joining the red-diamond-blazed Otterkill Trail. It soon reaches the cascading Baby Brook and turns left to parallel the brook. The Otterkill Trail turns right and crosses the brook, but you should continue ahead along the yellow-blazed Jessup Trail, which climbs steadily along the brook. In the next three-quarters of a mile, you’ll climb about 700 feet.

After joining a woods road, the trail detours to the right to pass by a beautiful cascade. This is a good place to take a break. Continue ahead along the Jessup Trail, which soon reaches a junction with the red-on-white-blazed Barton Swamp Trail. The Barton Swamp Trail proceeds ahead and to the right, but you should turn left to continue on the yellow-blazed Jessup Trail.

Panoramic Viewpoints
The Jessup Trail now climbs – steeply in places – along a ridge formed of the unusual conglomerate bedrock, studded with pebbles of white quartz and pink sandstone, that is characteristic of Schunemunk Mountain. The trail winds through pitch pines and soon reaches the first in a series of panoramic viewpoints. The Hudson River may be seen to the northeast, with the Newburgh-Beacon Bridge visible in the distance, and the East Hudson Highlands beyond. To the west, you can see the western ridge of Schunemunk Mountain.

Continue heading south along the ridge. After climbing another conglomerate outcrop, you’ll reach a second viewpoint. You’re high enough now that you can see over the western ridge of the mountain. The Shawangunks are visible in the distance to the northwest, and on a clear day, you can see the Catskills beyond.

After descending slightly and passing through an area with deciduous trees, the Jessup Trail climbs again and reaches a third viewpoint at a junction with the white-blazed Sweet Clover Trail. This is the highest and broadest of the three viewpoints on this section of the Jessup Trail, and you’ll want to pause and take in the panoramic 270E view.

Barton Swamp
When you’re ready to continue, turn right onto the white-blazed Sweet Clover Trail, which soon begins to descend. After climbing over a few minor ridges, the trail passes through dense mountain laurel thickets, and the descent steepens. At the base of the descent, you’ll cross Baby Brook (the crossing can be a little tricky when the water is high) and reach a junction with the red-on-white-blazed Barton Swamp Trail.

Turn left and follow the Barton Swamp Trail as it proceeds south along a nearly level route between the two ridges of Schunemunk Mountain. After about 1.3 miles, the blue-on-white-blazed Western Ridge Trail joins from the right. When the two trails diverge a short distance beyond, turn left, now following the blue-on-white blazes of the Western Ridge Trail.

The Western Ridge Trail steeply climbs the eastern ridge of the mountain. After a very steep pitch, the trail turns right along a ledge and reaches a panoramic west-facing viewpoint. You’ll want to take a short break here to catch your breath and enjoy the view! The trail continues to climb more gradually. Where it proceeds over bare rock surfaces, the trail is marked with blue paint blazes on the rocks and with cairns (small piles of rocks). After traversing an open area of exposed conglomerate bedrock, the Western Ridge Trail ends, on the crest of the eastern ridge, at a junction with the yellow-blazed Jessup Trail and the teal-diamond-blazed Highlands Trail.

The Megaliths
Turn left and follow the joint Jessup/Highlands Trail, which soon reaches the 1,664-foot-high summit of Schunemunk Mountain (marked on the rock with white paint), which affords a 360̊ view. The Jessup Trail bears left and descends, almost immediately reaching a junction with a white-blazed side trail (also marked by cairns) that leads to the Megaliths – a group of huge blocks that have split off from the bedrock. This is another good place for a break, as the interesting geologic features are complemented by a fine viewpoint to the west.

When you feel rested, return to the Jessup/Highlands Trail and turn left. In another third of a mile, the black-on-white-blazed Dark Hollow Trail leaves to the right. Turn right onto the Dark Hollow Trail, which crosses several small streams and soon begins a steady descent. The first part of the descent is quite steep, after which the trail crosses Dark Hollow Brook, bears left and reaches a short level stretch. Just before the descent resumes, there is another great view to the east and northeast over the Hudson River and East Hudson Highlands.

After another steep stretch, you’ll cross a brook and bear left again. Soon, the trail joins a woods road, which it follows for most of the remainder of the descent. At one point, the trail proceeds straight ahead, cutting off a loop of the road. The final viewpoint of the hike is reached as the trail begins a steep descent to rejoin the woods road.

The Dark Hollow Trail ends at the base of the descent, just before the railroad tracks. Turn left onto the red-blazed Otterkill Trail, which descends to cross Dark Hollow Brook below an attractive waterfall, then climbs to reach a junction with the white-blazed Sweet Clover Trail. Turn right onto the Sweet Clover Trail and cross the railroad tracks (use extreme caution, as the crossing is on a curve in the tracks, and it is difficult to see or hear approaching trains). Continue to follow the Sweet Clover Trail as it descends through the woods, turns right onto a woods road, then bears left and follows a grassy road through fields. When you reach the junction with the yellow-blazed Jessup Trail, turn right, then left, following the joint Sweet Clover/Jessup Trails back to the parking area where the hike began.