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Mt. Misery/Hill of Pines/Rattlesnake Hill/Black Rock Mountain Loop
This loop hike parallels a cascading stream and climbs to several panoramic viewpoints.
Moderate to Strenuous
Allowed on leash
Trail Conference volunteers maintain trails in this park.
Take the Palisades Interstate Parkway to its northern terminus at the Bear Mountain Bridge and continue north on US 9W for 8.8 miles. About half a mile after passing a parking area marked with a blue sign, turn right onto Mountain Road. Immediately, turn right again and proceed through a very narrow underpass beneath US 9W (large vehicles may not fit in this underpass). Continue ahead for 0.2 mile to a parking area on the right side of the road, just before a locked gate.
From the bulletin board at the end of the parking area, proceed ahead on the red-blazed Duggan Trail. In about half a mile, the red trail ends at a junction with the blue-blazed Reservoir Trail. Continue ahead on the blue trail, which immediately crosses Ben's Bridge (a wooden footbridge) and climbs along a picturesque stream, with cascades and waterfalls, following an old woods road. When the blue trail ends, bear right and continue ahead on the yellow-blazed Stillman Trail.
Soon, the Stillman Trail reaches the dirt White Oak Road. Here, it is joined by the teal-diamond-blazed Highlands Trail, which comes in from the left. The joint Highlands/Stillman Trails now turns right and follows the road for 100 feet, then turns left and begins a steep climb of Mt. Misery on a footpath. At the top, you’ll reach a viewpoint to the west and northwest which is partially obscured by trees. Continue ahead for a short distance, and you’ll come to a much better viewpoint, with Black Rock Mountain visible directly ahead, and Aleck Meadow Reservoir below to the left. You’ll want to stop here for a few minutes to savor the view and take a break from your arduous climb (you’ve climbed nearly 700 feet from Ben’s Bridge).
Continue ahead on the yellow/teal diamond trail, which begins its descent of Mt. Misery, first gradually and then more steeply. In a rocky area at the base of the descent, you’ll notice a triple white blaze, which marks the start of the Scenic Trail. Turn left and follow the white-blazed Scenic Trail, which crosses the blue-blazed Swamp Trail at the end of the rocky area and begins a steady climb of the Hill of Pines, passing through attractive mountain laurel and hemlock.
At the top of the climb, the trail comes out on open rocks, with a spectacular west-facing view. Black Rock Mountain may be seen on the right, and the Black Rock Forest fire tower is to its left. (Despite the name "Hill of Pines," there are only two pine trees near the summit, which is mostly covered with oaks). You’ll want to spend some time at this magnificent vantage point.
The trail climbs a little to the true summit, descends the hill, and soon crosses the dirt Carpenter Road diagonally to the right. It now begins a gradual climb of Rattlesnake Hill. After about ten minutes, you’ll reach a viewpoint to the right of the trail (the best view is from a rock ledge adjacent to a large pine tree). The fire tower may be seen straight ahead, and Bog Meadow Pond is to the left. After a short but steep descent and a relatively level stretch, you’ll reach a second viewpoint – this one marked by a cairn and a gnarled, nearly horizontal pine tree. Continue ahead through a dense mountain laurel thicket to the third viewpoint on Rattlesnake Hill, which offers a panoramic view from open rocks. Bog Meadow Pond is below on the left, with the rolling hills of Orange County beyond.
After pausing to enjoy the view, continue ahead on the white trail, which begins to descend, first steeply, then more gradually. The trail briefly runs along the southern boundary of Black Rock Forest, with Bog Meadow Pond visible through the trees to the left. After crossing the inlet stream of the pond, the trail reaches the dirt Bog Meadow Road. Turn left and continue along the road, which is marked with the white blazes of the Scenic Trail.
After about five minutes, you’ll reach a junction with the yellow-blazed Tower Vue Trail, marked by a cairn. This junction – which is easily missed – is just before a large rock outcrop. Turn right and follow the Tower Vue Trail over undulating terrain, through mountain laurel with an understory of blueberry. In about a third of a mile, there is a view through the trees of the fire tower from a rock ledge to the left of the trail. The trail now begins to run above Arthurs Pond, with views of the pond through the trees on the left.
When the Tower Vue Trail ends at the northern tip of the pond, by the dam, turn left onto the white-blazed White Oak Trail, cross below the dam, and continue along a gravel road. Soon, the White Oak Trail reaches Continental Road at a T-intersection. Turn right onto the road, continuing to follow the white blazes, but when the white blazes turn left and leave the road, proceed ahead on the road. Just beyond, you’ll come to a junction, marked by a huge white oak tree. Here you should continue ahead on Continental Road, as White Oak Road leaves to the right.
In another third of a mile, you’ll reach a complex intersection, with a cable barrier straight ahead. Turn right and continue on the yellow-rectangle-blazed Stillman Trail (also the route of the teal-diamond-blazed Highlands Trail). Just ahead, as the woods road bears left, bear right and follow the yellow and teal diamond blazes, which begin a gradual climb of Black Rock Mountain on a footpath.
After a short but very steep climb, you’ll reach the summit of the mountain (1,410 feet) amid scrub oak and pitch pines. The panoramic view from the summit includes Schunemunk Mountain and the Metro-North Railroad’s Moodna Viaduct to the west, and the Hudson River (crossed by the Newburgh-Beacon Bridge) to the northeast. Again, you’ll want to take a break to appreciate the view – the broadest of the entire hike.
The trail turns right and descends gradually. With the wide White Oak Road visible ahead, the trail bears left and joins a woods road. A short distance beyond, the yellow and teal-diamond blazes turn right, but you should continue ahead on the road, now following the white-blazed Black Rock Hollow Trail. This trail continues to descend along the road, with portions rerouted to bypass very eroded sections of the road.
At the base of the descent, the white-blazed trail ends at a filtration plant. Turn right onto the blue-blazed Reservoir Trail and follow it around the plant and along the brook to a junction with the red-blazed Duggan Trail just before Ben’s Bridge. Turn sharply left onto the red-blazed trail and follow it uphill to the parking area where the hike began.