Cupsaw Mountain Loop from Shepherd Lake


This lollipop-loop hike parallels Cupsaw Brook, passing an attractive cascade, and climbs to a shelter on the ridge of Cupsaw Mountain.

2 hours
Easy to Moderate
2.5 miles
Route Type:
Allowed on leash
Waterfall, Fees
First Published:
Daniel Chazin



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Trailhead GPS Coordinates
Driving Directions

Take Skyline Drive to its northwestern terminus at Greenwood Lake Turnpike (County Route 511). Turn right, continue for 1.5 miles, and turn right onto Sloatsburg Road. Continue for 2.1 miles and turn right onto Morris Road. In 1.3 miles, just before the entrance to the Skylands section of Ringwood State Park, turn left onto Shepherd Lake Road and proceed for 0.8 mile to Shepherd Lake. Past the entrance booth, bear left and park in the designated parking area (a parking fee is charged from Memorial Day to Labor Day). NOTE: Shepherd Lake is a popular destination on summer weekends, and the parking area can fill up early in the day.

Walk back towards the entrance booth but turn right, just before reaching the booth, at a sign that designates the red-blazed Ringwood-Ramapo Trail. This trail is marked with both red-on-white metal blazes and solid red blazes on brown plastic wands. You’ll also notice many grey blazes on trees along the trail; these were used to obliterate the solid red paint blazes that formerly marked the trail. For the most part, the grey blazes do indicate the correct trail route. The trail enters the woods on a wide woods road, immediately crossing a seasonal stream. You may hear gunshot sounds in the distance. These come from the Thunder Mountain Shooting Range, located less than half a mile south of the Shepherd Lake parking area (you’ll be heading west and north, away from the range). Unfortunately, though, the sounds of gunfire can often be heard for much of the hike. In a short distance, follow the red-on-white blazed trail as it bears right, leaving the road, and descends on a rocky footpath towards Cupsaw Brook, the outlet of Shepherd Lake. As you reach the base of the descent, you’ll notice an interesting cascade to the right, just off the trail. The trail bears left, parallels the brook, then crosses it on a sturdy wooden bridge (built in 2006 as an Eagle Scout project). Just beyond the bridge, the blue-blazed Cupsaw Brook Trail joins from the right. Continue ahead, now following both red-on-white and blue blazes on a relatively level footpath. Soon, you’ll cross a seasonal stream on rocks adjacent to a large blowdown (the crossing might be difficult during periods of high water). In another quarter of a mile, you’ll come to a T-intersection with a woods road. Turn right and immediately cross another tributary stream on rocks. Just beyond, you’ll reach another junction, where the two trails separate. The Cupsaw Brook Trail continues ahead on the woods road, but you should turn right, now once again following only the red-on-white blazes of the Ringwood-Ramapo Trail. After crossing yet another tributary stream, you’ll pass an interesting cracked boulder to the left of the trail. The trail continues along a rocky footpath and soon begins to climb steadily. After passing some interesting boulders to the right, the trail briefly dips into a hollow, then continues to climb rather steeply to the top of the ridge of Cupsaw Mountain. Atop the ridge is a wooden shelter, built by the “Hiking, Eating, Arguing and Puzzle-Solving Club of the Cooper Union.” The land on which the shelter is located, purchased by the State of New Jersey in 1978, was formerly part of the Green Engineering Camp of the Cooper Union for the Advancement of Science and Art, of New York City. Although camping is no longer permitted at the shelter, and it is not well maintained, it is still the site of an annual gathering of the Cooper Union Alumni Association. After resting from the climb, continue ahead on the Ringwood-Ramapo Trail. In about 200 feet, you’ll reach a junction where the Ringwood-Ramapo Trail turns left, but you should continue ahead on a woods road, now following the yellow blazes of the Cooper Union Trail, which comes in from the left. The trail climbs briefly and then descends steadily along the road, with views of the mountains to the west through the trees when the leaves are down. Soon, the sounds of traffic on nearby Sloatsburg Road may be heard. Just before reaching the base of the descent, be alert for a triple-blue blaze on a tree to the left, which marks the start of the Cupsaw Brook Trail. Turn right and follow this blue-blazed trail, which climbs back up the ridge of Cupsaw Mountain, then descends rather steeply to a T-intersection with a woods road. Turn right onto the road, which levels off. Soon, you’ll reach another junction, where you again turn right. The trail briefly approaches Cupsaw Brook, then moves away from it. After some more level walking, you’ll return to the junction where the Cupsaw Brook Trail intersects the red-on-white-blazed Ringwood-Ramapo Trail. Turn left onto the Ringwood-Ramapo Trail and retrace your steps, crossing the wooden bridge over Cupsaw Brook and following the red-on-white blazes back to the parking area where the hike began.

Comment: Please be relevant, civil, non-commercial.

red trail obscured by blowdown

I just hiked this trail today and there is a significant blowdown when trying to follow the red trail up Cupsaw Mountain.  The trail markers seem to have all blown down and there is no longer a distinct trail up the mountain.  I hiked up to the large gneiss outcrop at the top and followed its ridgeline until it crossed the red trail and I continued the rest of the hike with no problem.  Bottom-Line: be prepared to do some bushwhacking up Cupsaw Mountain until the trail is cleared and new trail markers are posted.