This loop hike climbs to viewpoints from the summit of Black Rock Mountain and passes the historic Hogencamp, Pine Swamp, Surebridge and Boston Mines.
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Take N.Y. Route 17 north through Sloatsburg and Tuxedo. About 2.4 miles north of Tuxedo, take the exit leading to N.Y. Route 17A. Turn right at the top of the ramp onto County Route 106 and continue for 2.2 miles to a Hikers' Trailhead Parking Area on the right side of the road, just beyond a sharp curve.
From the parking area, cross the road and turn left on the White Bar Trail, blazed with white horizontal rectangles. The White Bar Trail parallels the road for about 500 feet, then turns right and crosses a stream on a metal culvert. A short distance beyond, it bears right at a fork (the road that goes off to the left will be your return route) and continues ahead on a woods road.
In another quarter of a mile, you'll reach a junction with the Nurian Trail. Both trails are blazed white, but the rectangular blazes of the Nurian Trail are vertical, rather than horizontal. Turn right and follow the Nurian Trail, which descends to cross a stream on rocks. After briefly paralleling the stream in a hemlock grove, the trail bears left and ascends rather steeply. Several steep pitches alternate with more moderate sections. In about half a mile, the Nurian Trail ends on the ridge of Black Rock Mountain, at a junction with the red-dot-on-white-blazed Ramapo-Dunderberg (R-D) Trail.
Turn left and follow the red-and-white-blazes along the rocky ridge of Black Rock Mountain. In a few minutes, you'll reach an expansive west-facing viewpoint from open rocks to the left of the trail. As the trail continues along the ridge, you'll pass an area scarred by a recent ground fire. In places, the route is marked by cairns (small piles of stones) in addition to paint blazes.
After about a mile of pleasant ridgetop walking, with some ups and downs, you'll come to a flat area of open rocks, known as Bald Rocks. Just to the left of the trail is a rock outcrop that marks the highest spot in Harriman State Park (elevation 1,382 feet). Two cairns point the way to this outcrop, which offers excellent views to the west, but the trail itself (marked by paint blazes on the rocks) bears right and continues northeast along the main ridge. Just beyond, you'll notice the Bald Rocks Shelter to the right. This shelter - built out of huge granite slabs - was constructed in 1933.
At the base of a short descent, the R-D Trail reaches a junction with the yellow-blazed Dunning Trail. Turn right onto the Dunning Trail, which follows the route of an old mining road, known as the Crooked Road. After crossing a stream, it traverses a level area of bare rock dotted with boulders, known as the Bowling Rocks.
About a mile from the junction with the R-D Trail, the Dunning Trail curves to the north and passes remnants of the Hogencamp Mine, which operated from 1870 to 1885. On the left side of the trail, you'll notice a water-filled mine shaft, about 25 feet in diameter, with a seven-inch cast-iron pipe (once used to dewater the mine) jutting out of the water. Use extreme caution when approaching this shaft! On the opposite side of the trail, iron rods may be seen protruding from a crumbling concrete base (now covered with grass), with a stone-lined well, three feet in diameter, beyond. A short distance ahead, there is a stone platform to the right. It was built out of tailings - the technical term for the pieces of rock discarded during the mining process. Piles of tailings may be found throughout this mining site.
After crossing a stream, you'll notice old stone foundations to the right. These are the remains of a village that once housed the miners. Just beyond, the aqua- blazed Long Path joins from the left and then leaves to the right. Continue ahead on the yellow-blazed Dunning Trail. In another half a mile, you'll pass the interesting Pine Swamp on the right. To the left, you'll notice a huge pile of tailings - a remnant of the Pine Swamp Mine, opened in 1830 and worked intermittently until about 1880. A long, narrow mine opening may be seen to the left of the trail, just south of a stream that crosses the trail a short distance ahead.
About 500 feet beyond this mine opening, you'll reach the triple yellow blaze that marks the end of the Dunning Trail. Turn left and follow the red-triangle-on-white Arden-Surebridge (A-SB) Trail, which climbs gradually on another old mining road. In half a mile, you'll reach a trail junction known as "Times Square" (the name is painted on a boulder to the right.) Continue ahead, now following both the A-SB Trail and the aqua-blazed Long Path. When the red-on-white and aqua blazes leave to the left, continue ahead on the grassy woods road you have been following, known as the Surebridge Mine Road. The next section of the road can be flooded at times, and you may end up getting your feet a little wet. The road continues through mountain laurel and rhododendron, with the attractive Surebridge Swamp to the left.
Near the end of the swamp, you'll notice another mine pit to the right of the trail. This is a remnant of the Surebridge Mine, active during the Civil War period. In another 500 feet, you'll reach a junction (marked by a cairn) with the Bottle Cap Trail, which features white bottle caps as blazes. Turn left and follow this trail across a stream, up to the ridge of Surebridge Mountain and down through a hemlock grove to rejoin the A-SB Trail/Long Path. Continue ahead, following the aqua and red-triangle-on-white blazes, for only about 300 feet. Just after crossing a swampy area on rocks, look carefully for three horizontal white blazes to the left. Turn left and follow the White Bar Trail southward.
The White Bar Trail soon joins a woods road, which it follows south through a pleasant valley. After about a mile, the yellow-blazed Dunning Trail joins from the left. When the Dunning Trail leaves to the right, follow the yellow blazes. The Dunning Trail goes down to a valley - passing a large cliff on the way - then climbs to a ridge, from where it descends to the base of the Boston Mine. This mine -- a large open cut into the hillside, partially filled with water -- is reached by a short path to the right. It was last worked around 1880.
Continue ahead on the Dunning Trail, which soon turns left and begins to follow Island Pond Road, a woods road. When the yellow blazes turn off to the right a short distance ahead, continue ahead, following Island Pond Road, which leads back to a junction with the White Bar Trail just west of the parking area on Route 106 where the hike began.