Hike Description:

Proceed ahead, passing through an opening in a stone wall by a “Do Not Enter” sign. Immediately turn right, passing brown signs that mark the trailheads of the white-blazed Crossover Trail and the red-on-white-blazed Ringwood-Ramapo Trail. 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, turn left onto a footpath, soon 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 turn left, continuing to follow the red-on-white-blazed Ringwood-Ramapo Trail, which follows a level route along the side of the hill. Soon, the orange-blazed State Line Trail begins on the left. Continue to follow the Ringwood-Ramapo Trail, which 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 and the white-blazed Crossover Trail.

Just ahead, immediately after crossing a small stream on a footbridge, follow the Ringwood-Ramapo and Cupsaw Brook Trails as they turn left, leaving the Crossover Trail. Soon, the joint trails cross a small stream on rocks. After paralleling Cupsaw Brook, 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 the 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-on-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 pink-on-white-blazed Five Ponds Loop comes in from the right and briefly joins the Ringwood-Ramapo Trail. You will soon head down the mountain on the Five Ponds Loop, 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 Garden at Skylands Manor may be seen in the foreground, with the Wyanokies in the distance. The Wanaque Reservoir is visible on 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 Five Ponds Loop. Turn left (west), following the pink-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 pink-on-white-blazed trail, which follows a series of gradual switchbacks – the remnants of an old carriage road. At the base of the descent, turn right onto the white-blazed Crossover Trail, which follows a gravel road along the base of the mountain. You will be following the Crossover Trail for the rest of the hike. 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. Turn right into the parking area and proceed to the northwest corner, where you will see a sign for the Crossover Trail. Continue on a footpath through a meadow, then enter the woods and soon begin to descend on switchbacks. This trail section, built by the Jersey Off-Road Bicycle Association, was designed primarily for mountain bikes. It features very gentle grades and switchbacks that may seem excessively long to hikers.

After crossing the paved Shepherd Lake Road diagonally to the right and then crossing the route of a gas pipeline, the trail continues to descend on switchbacks. At the base of the descent, it turns right onto a woods road. It follows the road for a short distance, then turns left, leaving the road, and continues to descend on a footpath. Soon, it turns right onto another woods road, which it follows across a stone causeway and a footbridge over Cupsaw Brook.

Just ahead, the red-on-white-blazed Ringwood-Ramapo Trail and the blue-blazed Cupsaw Brook Trail join from the right, and all three trails cross a tributary stream on a footbridge. (You were at this location earlier in the hike, when you crossed the bridge in the opposite direction.) About 50 feet beyond the bridge, follow the white-blazed Crossover Trail as it turns left, leaving the other two trails, and begins to ascend very gradually.

At the crest of the rise, the Crossover Trail turns right. Here, a side trail, blazed with a black dot on white, begins on the left. A short distance ahead, the yellow-blazed Cooper Union Trail, which follows a woods road, crosses. Continue along the Crossover Trail, which soon begins to descend on switchbacks.

At the base of the descent, the white-blazed trail turns onto a relatively level woods road, which it follows 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.