Hike Description:

This hike follows a combination of footpaths, carriage roads (built for the estates that once dominated this area) and a mountain bike trail. Created primarily for bicyclists, the mountain bike trail - part of which is a narrow, "single-track" route - is also open to hikers. However, hikers should be alert for bicycles and, although park rules provide that bicyclists must yield to hikers, hikers may choose to step off the trail and allow bicyclists to pass.

From the parking area, follow the paved path down to the beach on Shepherd Lake. Continue past the boat launch parking area and the boat house, with the lake to your left. Just beyond the boat house, you’ll notice a kiosk, where an orange-blazed trail begins. Continue on a gravel road along the lake, following both the orange blazes and the red-on-white blazes of the Ringwood-Ramapo Trail. 

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. This will be your return route, but for now, continue ahead on the red-on-white-blazed trail, which passes an old stone foundation on the left. A short distance beyond, the trail crosses a gas pipeline (the many plastic tubes you see along the pipeline contain seedlings, part of an effort to remediate the area). The trail now climbs the northern shoulder of Mount Defiance, first gradually, then more steeply. Just below the 1,040-foot summit, there is a limited view to the west over Ringwood Manor and the Cupsaw Lake area. 

After a short but steep descent, the trail follows the crest of the ridge, paralleling impressive cliffs on the right and passing an interesting split boulder. Soon, you’ll reach a junction with the pink-on-white-blazed Five Ponds Loop. You will be continuing ahead on the Ringwood-Ramapo Trail, but for now, turn right onto the Five Ponds Loop.

In about 500 feet, as the trail bears left and begins a steady descent, you’ll notice an unmarked trail on the right. Follow this trail, which heads slightly uphill to a panoramic west-facing viewpoint. Skylands Manor may be seen directly below, surrounded by the exotic trees of the New Jersey State Botanical Garden. The Monksville Reservoir is directly ahead, and the Wanaque Reservoir is visible to the left (south) through the trees.

After taking in the view, return to the Ringwood-Ramapo Trail and turn right. In about 350 feet, there is another west-facing viewpoint from a rock outcrop to the right. The view of Skylands Manor is largely obscured by trees, but you get a better view of the Wanaque Reservoir.

Continue south on the Ringwood-Ramapo Trail, which descends gradually on a winding footpath. Soon, it reaches a junction where the blue triangle-on-white Skylands Trail begins on the left. Bear right to continue on the Ringwood-Ramapo Trail, which heads south along the ridge of Mount Defiance. After crossing a wide carriage road, the trail levels off and traverses open rock ledges. It recrosses the carriage road, passes a balanced boulder on the left, and descends gradually until it once again reaches the carriage road. Turn left just beyond the carriage road, leaving the Ringwood-Ramapo Trail, and follow the white-blazed Crossover Trail, which descends gradually on switchbacks.

Near the base of the descent, the Crossover Trail crosses a wide gravel road, descends a little more, and turns right onto another gravel road, joining the pink-on-white-blazed Five Ponds Loop. The joint Five Ponds Loop/Crossover Trail now crosses a bridge over a stream. In 100 feet, follow the joint Five Ponds Loop/Crossover Trail, which turns left, leaving the carriage road, then switches back and heads south along the hillside.

The trail heads uphill, goes around a switchback, and then continues gently uphill on an attractive footpath, constructed by the Jersey Off-Road Bicycle Association (JORBA). After passing a balanced rock on the left and crossing a woods road, you'll reach the crest of a rise. Here, the Crossover Trail leaves on the left, but you should continue ahead, following the Five Ponds Loop. Just beyond, the Five Ponds Loop joins a woods road that comes in from the right. The road curves to the right, climbing gradually.

Be alert for a right turn, where the Five Ponds Loop leaves the road and climbs more steeply on a footpath. After a short climb, it turns right onto a woods road. Just ahead, there is a viewpoint on the left over Gatun Pond, a good spot to take a break. 

Continue ahead on the road, climbing gently, and bear right at a fork. When you reach the next intersection, continue to follow the pink-on-white blazes. A short distance beyond, you’ll reach a four-way intersection, where you turn left, then bear right just ahead and descend to Brushwood Pond, crossing a woods road along the way. At the base of the descent, a short side trail on the right leads to a view of the pond.

The Five Ponds Loop now emerges onto a large field (on weekends, you may notice illegal use of this area by all-terrain vehicles). Continue across the field. Towards the northern end of the field, you'll notice a pink-on-white blaze on a tree to the right. Turn right and continue along a woods road. To avoid a flooded section of the road, the Five Ponds Loop bears right onto a footpath, then joins another road. After crossing between two small ponds, the road climbs a little.

Just ahead, follow the Five Ponds Loop as it turns right onto a footpath, leaving the road and rejoining the Crossover Trail. The footpath soon ends at a T-intersection with the woods road just south of Weyble Pond. Follow the pink-on-white and white blazes as they turn right, rejoining the road, and follow the road around the southern end of the pond. In a short distance, the Crossover Trail leaves to the right. Just ahead, a rock ledge on the left, below the road, offers a view over Weyble Pond.

Continue to follow the Five Ponds Loop as it heads north on the woods road. The trail turns left at the next intersection, then bears right at the following intersection. About half a mile from Weyble Pond, the Five Ponds Loop turns left, leaving the woods road, and heads downhill.

At the base of the descent, the Five Ponds Loop crosses a woods road, turns right, then immediately rejoins the woods road. It now passes between the two Glasmere Ponds, with good views over the northern pond.

Just beyond, you’ll reach a T-intersection. Here, the Five Ponds Loop turns left, but you should turn right, now once again following the mountain bike trail. The carriage road that you are following soon goes by the ruins of a frame building on the left and passes between two stone pillars, with abandoned stone buildings (originally, the gate houses for the estate) on each side of the trail. Just beyond, bear left at the fork.

A short distance ahead, at the top of a rise, the mountain bike trail leaves the road (a brown wand is visible about 25 feet into the woods). Turn left and follow this “single-track” mountain bike trail, which will take you back to Shepherd Lake. Although not marked (except with occasional brown wands at intersections), the trail is well-defined and easy to follow. It climbs on switchbacks to cross the gas pipeline and the Ringwood-Ramapo Trail, then continues to climb a little more. After reaching a high point, it descends gradually, crosses a woods road, and once again approaches the gas pipeline (although it does not cross it). The mountain bike trail then heads north to end at the Ringwood-Ramapo Trail along the shore of Shepherd Lake. Turn left and follow the Ringwood-Ramapo Trail back to the parking area at the southwest corner of the lake, where the hike began.