Know the New Hiking How-tos
Monks Trail Circular
Directions to trailhead
Take Interstate Route 287 to Exit 57 and continue on Skyline Drive to its western end at Greenwood Lake Turnpike in Ringwood. Turn right and proceed for about four miles to Margaret King Avenue. Continue ahead along Greenwood Lake Turnpike for another 0.3 mile and turn left into the access road leading to the northern boat launch area for the Monksville Reservoir. The access road is just east of the Monksville Reservoir and directly opposite Beech Road. Continue along the access road for about 0.2 mile to the parking area.
At the southern end of the parking area, a yellow gate with a triple white blaze marks the start of the Monks Trail. You’ll be following this trail for the entire hike. Proceed ahead for 50 feet, then turn left, following the white-blazed trail into the woods (the trail to the right, also blazed white, will be your return route).
The trail continues along the hillside, parallel to the Monksville Reservoir (visible below through the trees). As it approaches Greenwood Lake Turnpike, the Monks Trail passes the start of the green-blazed Monks Connector Trail and turns right onto a woods road. Soon, it turns right again on a wider woods road and begins to climb. After passing a large rock outcrop to the right, the trail levels off. It goes under a power line and then crosses a gas pipeline.
Just beyond the pipeline crossing, as the trail begins to descend, look carefully to the left. You will notice two large open pits, about 100 feet from the trail. These are the remnants of the Winston Iron Mine, which was opened shortly after the Civil War and abandoned by 1880. You’ll also see piles of mine tailings and other smaller pits nearby.
Just ahead, the woods road curves to the left, but you should follow the white-blazed trail as it turns right, leaving the road, and continues on a footpath through the woods. After crossing a stream, the trail proceeds along a narrow ridge, continues through a rocky area, and descends slightly. Near the base of the descent, the yellow-blazed Highland Meadow Trail joins from the left. Just beyond, you will see two smaller mine openings on the left, which are often flooded. As the trail continues ahead, the Monksville Reservoir is visible through the trees.
About a mile from the start, the trail turns right at a T-intersection. Here, the yellow-blazed Highland Meadow Trail leaves to the left. Soon, a short black-dot-on-white-blazed side trail leads left to the parking area at the southern boat launch site, and the Monks Trail turns right. The trail now begins a steady ascent of Monks Mountain on a winding footpath, climbing about 300 vertical feet in the next quarter of a mile. As the trail levels off at the top of the climb, a side trail -- blazed black-dot-on-white -- leaves to the left. Follow this side trail, which passes a rocky cedar-studded high point and descends slightly to reach a viewpoint over the Monksville Reservoir in 300 feet. The Monksville Dam is visible to the left, with Harrison Mountain in the background.
Now return to the main trail and turn left. After a relatively level stretch along the ridge, the trail climbs a little and passes just to the left of a high point on Monks Mountain. A short distance beyond, it begins a steady descent on a rocky footpath, rather steeply in places, passing a large lichen-covered rock outcrop on the right. After leveling off in a broad valley, the trail bears right and continues to descend gradually.
The trail soon crosses under overhead power lines, bears right and begins to parallel the reservoir. It climbs a little, crosses a woods road, then turns left and crosses a gas pipeline diagonally to the left. The trail now bears right and follows a footpath parallel to the shore of the reservoir. In a quarter mile, you’ll return to the parking area where the hike began.