Timp-Torne/Dunderberg Spiral Railway/R-D Trail Short Loop from Route 9W

From the parking area, walk south on Route 9W for a few hundred feet. Just beyond road signs for Routes 9W and 202, you'll see three blue blazes and three red-dot-on-white blazes on a tree adjacent to the road. These blazes mark the start of the Timp-Torne (blue) and Ramapo-Dunderberg (red-dot-on-white) trails. You'll be following the Timp-Torne Trail for the first part of the hike and returning on the Ramapo-Dunderberg Trail.

Follow the blue and red-dot-on-white blazes into the woods along a level footpath through an area of tangled vines. Soon, the trail will bear left and climb stone steps, and you'll reach a stone-arch tunnel to the left. This tunnel is a remnant of the Dunderberg Spiral Railway, the construction of which commenced in 1890. The plan was to have the rail cars pulled up the mountain on a cable incline by a stationary steam engine, with the downhill journey being made by gravity. Large sums were spent on the project, two tunnels were partially completed, and much of the line was graded, but the promoters ran out of funds, and the railway was never finished. The tunnel you see to the left was designed to allow the ascending trains to pass over the route of the descending trains.

The trail now bears right and ascends more steeply on switchbacks and stone steps. At the top of the climb, you'll reach a junction. Here, the red-dot-on-white blazes continue ahead, while the blue blazes turn left. Follow the blue blazes of the Timp-Torne Trail, which head southwest, parallel to the river. The trail continues to climb, but on a more moderate grade, with views of the river through the trees.

In another ten minutes, the trail turns right and heads away from the river. After going through a rocky area on switchbacks, you'll arrive at a graded section of the railway. Follow the blue blazes as they turn left and continue along this level, graded embankment for the next quarter of a mile. With the railbed ahead blocked off by a fallen tree, the trail turns right and climbs to the next higher level, where it turns left. Just ahead you'll come to the portal of an unfinished tunnel, intended for use by the descending trains.

The trail now returns to the lower level of the graded railway, which it follows around a curved embankment, with views over the Hudson River. The curved roadbed ends at the opposite end of the uncompleted tunnel, but the trail bears left, crosses a stream and reaches a woods road.

Turn right and follow this road, known as the Jones Trail. In about a third of a mile, after once again crossing the stream, you'll reach a junction with another grade of the railway. Turn left and follow the unmarked railway grade for about a quarter of a mile to a T-intersection with the red-dot-on-white-blazed Ramapo-Dunderberg Trail.

Turn right onto Ramapo-Dunderberg Trail, which climbs to a high point with a view, descends slightly, then climbs steeply to reach an even better viewpoint. You can see the Hudson River to the right (south), with Bear Mountain and the Bear Mountain Bridge to the left (north). Continue along the ridge of Dunderberg Mountain, passing through thickets of dense birch saplings.

After descending from the ridge, steeply in places, you'll notice a viewpoint from a rock outcrop just to the right of the trail, with Peekskill directly across the river. A short distance beyond, as the trail curves to the right, a short white-blazed trail leads ahead to another viewpoint. The trail soon joins another graded section of the railbed, with several gaps where the grading was never finished, and passes more views over the Hudson River.

At a stone abutment (built to carry the cars going up the mountain), the trail turns sharply left and descends steadily along the right-of-way excavated for the cable incline. After about ten minutes, you'll reach a junction with the blue-blazed Timp-Torne Trail. Continue ahead, following both blue and red-dot-on-white blazes back to the parking area where the hike began.