Hike Description:

From the parking area, proceed ahead (east) on Otterkill Road for 0.2 mile. About 150 feet before reaching the massive Moodna Viaduct (which spans the valley to the left), turn right onto a footpath, following the white-blazed Trestle Trail, which proceeds uphill rather steeply on a woods road, with the Moodna Viaduct to the left.

In about 500 feet – just before reaching the level of the viaduct – you’ll arrive at a fork in the trail. Here, the red-blazed Otterkill Trail begins on the left. Bear left and follow the Otterkill Trail. A short distance ahead, you’ll reach a sweeping east-facing view, with the railroad tracks visible in a rock cut below. The trail continues parallel to the railroad over undulating terrain.

In about a mile, the Otterkill Trail turns left onto an intersecting woods road and descends to cross the cascading Baby Brook on a wooden footbridge. On the south side of the brook, you’ll reach a junction with the yellow-blazed Jessup Trail. Turn right and follow the 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.

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. This unusual rock has been smoothed by glacial action, sometimes resembling a level sidewalk. 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. As you climb another conglomerate outcrop, you’ll pass several more panoramic viewpoints. 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 passing through an area with deciduous trees, the Jessup Trail climbs again and reaches yet another viewpoint at a junction with the white-blazed Sweet Clover Trail. This is the highest and broadest of the viewpoints on this section of the Jessup Trail, and you’ll want to pause and take in the panoramic 270-degree view.

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.

Continue ahead on the white-blazed Sweet Clover Trail, which climbs rather steeply to the crest of the western ridge of Schunemunk Mountain. Here, the Sweet Clover Trail ends, and you should turn left onto the orange-blazed Western Ridge Trail, which heads south along the western ridge of the mountain. The trail climbs to a panoramic viewpoint, with views both to the west and over the eastern ridge of the mountain, separated from the western ridge by the valley of Baby Brook.

Proceed ahead on the orange-blazed Western Ridge Trail, passing more viewpoints, as well a fascinating deep fissure in the rock to the right of the trail. After a brief descent, you’ll reach a junction with the blue-dot-on-white-blazed Ridge-to-Ridge Trail. Turn left, leaving the Western Ridge Trail and follow the Ridge-to-Ridge Trail, which descends to the valley. Here, it turns right onto a woods road, briefly joining the red-dot-on-white-blazed Barton Swamp Trail.

When the two trails diverge a short distance beyond, turn left, now following the blue-on-white blazes of the Ridge-to-Ridge Trail. The Ridge-to-Ridge Trail crosses a wet area on logs and 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 Ridge-to-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.

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), with limited views. The Jessup Trail bears left and descends, soon 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, passing some interesting cliffs on the way. 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. To the southeast, you can see Bear Mountain, with the Perkins Memorial Tower clearly visible on its summit.

After another steep stretch, you’ll cross a brook and bear left again onto a relatively level trail. Soon, the trail joins a woods road and resumes its descent. The trail follows the woods road for most of the remainder of the descent, but 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, which joins from the left.

A short distance ahead, the Sweet Clover Trail leaves to the right, but you should continue ahead on the Otterkill Trail, which will lead you back to the start of the hike in about two miles. After about a mile, the Otterkill Trail briefly joins the yellow-blazed Jessup Trail. When the Jessup Trail bears left, parallel to the cascading Baby Brook, continue to follow the Otterkill Trail as it turns right and crosses the brook on a wooden footbridge. You’re now retracing the route you followed at the start of the hike. When the Otterkill Trail ends at a junction with the white-blazed Trestle Trail, turn right onto the Trestle Trail, follow it down to Otterkill Road, then turn left onto Otterkill Road and continue to the parking area where the hike began.