Hike Description:

To get started on the Shepherd Lake/Mount Defiance/Skylands Manor Loop, proceed ahead, passing through an opening in a stone wall by a “Do Not Enter” sign. Immediately turn right, crossing a grassy area. Continue across an old concrete bridge over the Ringwood River (this was the original entrance to the Ringwood Manor estate). At the end of the bridge, white and red-on-white blazes on a brown wand mark the start of the Crossover and Ringwood-Ramapo Trails. Proceed ahead on a footpath, crossing the heavily-traveled Sloatsburg Road. The trails turn left and parallel the road, bear right and climb gently on switchbacks, then continue along the side of the hill, parallel to the road below.

After climbing on another switchback, you’ll reach a junction where the white-blazed Crossover Trail leaves to the right. This will be your return route, but you should continue ahead on the red-on-white-blazed Ringwood-Ramapo Trail. Soon, you’ll join the former trail route, which comes in from the left. The Ringwood-Ramapo Trail now continues its ascent of Cupsaw Mountain on a steeper grade. As the trail nears the crest of the ridge, the climb steepens.

At the ridgetop, the yellow-blazed Cooper Union Trail joins from the right, and both trails run jointly for 200 feet, descending to a woods road. Here, the Cooper Union Trail leaves to the left, but you should continue to follow the Ringwood-Ramapo Trail, which turns right, soon reaching an old shelter, in poor condition. The shelter was built by “The Hiking, Eating, Arguing and Puzzle-Solving Club of the Cooper Union” (this land, now part of Ringwood State Park, was once owned by Cooper Union). The trail now descends into a valley, climbs a little, then descends into a rocky valley where it crosses a stream and turns left onto a woods road, joining the blue-blazed Cupsaw Brook Trail. 

Follow the joint trails, which cross a stream on rocks, then immediately turn left, leaving the woods road. After crossing a stream on rocks and then paralleling it, the blue-blazed Cupsaw Brook Trail leaves to the left. Continue ahead on the Ringwood-Ramapo Trail, which turns right and crosses Cupsaw Brook on a wooden bridge. (From here on, the Ringwood-Ramapo Trail is marked by both red-on-white blazes and brown wands with solid red blazes). After passing a large cascade on the left, the trail bears right, away from the brook, and begins a steady ascent. At the top of the climb, the trail turns left onto a woods road and soon reaches a paved road at a traffic circle near Shepherd Lake. 

The trail turns right on the paved road, then immediately left, following the sign in the middle of the traffic circle for the boat launch. It continues through the boat launch parking area, then follows a paved road past a boathouse and a kiosk, where an orange-blazed trail begins. Continue by following a gravel road along the south shore of Shepherd Lake, marked with both red-on-white and orange blazes. 

In about a third of a mile, both trails turn right, leaving the road. Continue to follow the blazed trails, which head uphill on a footpath. At an intersection with a woods road, the orange-blazed trail turns left, but you should continue ahead, now following only the red-and-white blazes of the Ringwood-Ramapo Trail. 

The trail climbs to the top of a rise, then descends to cross a mountain bike trail. Continue ahead on the red-on-white-blazed trail, which passes an old stone foundation on the left. After crossing a gas pipeline (where many seedlings have been planted to remediate the area), the trail begins to climb the northern shoulder of Mount Defiance, first gradually, then more steeply.

After reaching the 1,040-foot summit, the trail descends steeply  and continues along the ridge, paralleling impressive cliffs on the right. At the end of the cliffs, the green-and-white-blazed Halifax Trail comes in from the right and briefly joins the Ringwood-Ramapo Trail. You will soon head down the mountain on the Halifax Trail, but for now, continue ahead for another 350 feet along the Ringwood-Ramapo Trail until you see a large rock outcrop to the right of the trail. 

Climb this outcrop, which is studded with cedar trees, to reach a panoramic view from the top. The New Jersey State Botanical Gardens at Skylands Manor may be seen in the foreground, with the Wyanokies in the distance. The Wanaque Reservoir is visible to the left. This is a good place for a break.

When you’re ready to continue, retrace your steps on the Ringwood-Ramapo Trail back to the junction with the Halifax Trail. Turn left (west), following the green-on-white blazes, which climb over a small rise and then level off. Just before the trail begins a steady descent, you’ll reach a fork. The trail heads left here, but you may wish to follow an unmarked path to the right which leads up to a rock outcrop with a view over the gardens of Skylands Manor.

Continue down the mountain on the green-on-white-blazed trail, which follows a series of gradual switchbacks – the remnants of an old carriage road. At the base of the descent, where the green-on-white trail ends, turn right onto the white-blazed Crossover Trail, which follows a gravel road along the base of the mountain. When you reach a paved road, turn right and follow the road through the grounds of Skylands Manor, passing an English Tudor guest house with a sundial clock on its chimney to the right.

Just beyond a greenhouse, you’ll reach a road junction at the entrance to Parking Area A. The double blaze seems to indicate a right turn into the parking area, but you should instead bear left (do not go into the parking area) and then immediately turn right and follow the park access road downhill, passing between two stone eagles that once adorned New York City’s Pennsylvania Station. After crossing an intersecting road, follow the white blazes as the trail bears left, reenters the woods, and descends steadily, passing through some wet areas. At the base of the descent, the trail crosses the route of a buried gas pipeline, turns right to parallel it, then turns left and reaches the paved Morris Road.

Turn left on the paved road, cross a stone-walled bridge over Cupsaw Brook, then follow the white blazes as they turn right and reenter the woods, passing a stone foundation on the right. The white-blazed Crossover Trail climbs gradually to reach a T-intersection with a woods road – the route of the yellow-blazed Cooper Union Trail. Turn left, briefly following the joint route of the two trails, then turn right at the next T-intersection and follow the white blazes along a relatively level woods road for about half a mile to a junction with the red-on-white blazed Ringwood-Ramapo Trail. Turn left and follow the joint Crossover and Ringwood-Ramapo Trails, retracing your steps back to the start of the hike.