Five Ponds Loop
Directions to trailhead
Take I-287 to Exit 57 and proceed north on Skyline Drive. At the end of Skyline Drive, turn right and follow Greenwood Lake Turnpike north for 1.5 miles to Sloatsburg Road. Turn right and follow Sloatsburg Road for 2.1 miles to Morris Avenue, then turn right and follow Morris Avenue for 1.4 miles to its end at the Skylands Manor section of Ringwood State Park. Pass between two stone eagles and continue past a toll booth (during the summer season, a parking fee may be charged). Proceed ahead and follow signs to Parking Lot C.
This hike loops around five ponds in Ringwood State Park -- Gatun Pond, Brushwood Pond, Weyble Pond, Glasmere Ponds and Swan Pond -- following woods roads and footpaths, and it climbs to a viewpoint at the crest of Mount Defiance. For much of the way, the hike follows multi-use trails, which are open to mountain bikes. The Five Ponds Loop was blazed in the fall of 2020 by volunteers of the New York-New Jersey Trail Conference.
You will notice triple pink-on-white blazes on both sides of Parking Lot C. Bear right (south) (do not begin at the kiosk) and follow the pink-on-white-blazed Five Ponds Loop up a woods road, bearing right at the fork. Soon, you'll join another woods road that comes in from the left, the route of the white-blazed Crossover Trail. The pink-on-white and white trails jointly climb gently on the woods road, then level off. After climbing a little more and curving to the left, you'll reach a junction with the red-on-white-blazed Ringwood-Ramapo Trail. Here, the Crossover Trail leaves to the right, but you should continue ahead on the woods road, now following only the pink-on-white blazes of the Five Ponds Loop.
The trail now begins to descend. Along the way, you'll pass on the left the start of the pink-with-black-stripe-on-white-blazed Five Ponds Connector, but continue ahead on the woods road. After curving to the right, you'll cross a gravel road at the base of the descent. The Crossover Trail is visible on the right here, but you should continue ahead. Just beyond, the Crossover Trail joins from the right. Both trails cross a stream and then bear left, leaving the woods road.
Follow the joint Five Ponds Loop/Crossover Trail, which head uphill, go around a switchback, and then continue 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 four-way intersection, turn left, then bear right just ahead and descend to Brushwood Pond. 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). Follow a dirt road along the right side of the field. About halfway through the field, you'll notice a double pink blaze on a post to the right. Turn right here 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. It immediately reaches a T-intersection, where it briefly turns left onto a woods road, then turns right and continues to descend on a footpath.
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. The trail goes around a gate and reaches an intersection with another woods road. It turns left and follows the road for 100 feet, then turns right onto a footpath and begins a steady climb of Mt. Defiance on switchbacks.
At the top of the climb, the Five Ponds Loop crosses the blue-triangle-on-white-blazed Skylands Trail and the red-on-white-blazed Ringwood-Ramapo Trail. A short distance beyond, as the Five Ponds Loop bears left, follow a short side trail, blazed with a black star on pink, which leads right to a west-facing viewpoint, with the hills of Tranquility Ridge County Park visible in the distance.
The Five Ponds Loop now descends steadily on switchbacks, following an old carriage road. At the base of the descent, the Five Ponds Loop turns left, joining the white-blazed Crossover Trail. Follow the Five Ponds Loop/Crossover Trail along a wide road for about a quarter mile. When you reach a fork in the road, bear right and continue on the pink-on-white-blazed Five Ponds Loop. Just beyond, a sign marks a short side trail on the right which leads to Swan Pond. After descending a little and passing a paved road that goes off to the right, the Five Ponds Loop turns left onto a gravel road. It crosses a bridge over a stream, bears right at a fork and continues to its end at Parking Lot C, where the hike began.