Round Hill/East Mountain Loop
Directions to trailhead
From the east end of the Bear Mountain Bridge, proceed north on N.Y. Route 9D for 8.0 miles to Peekskill Road at the southern end of Cold Spring (just beyond the Boscobel Restoration). Turn right and follow Peekskill Road for 0.5 mile to its terminus at a junction with N.Y. Route 301, then turn right and follow Route 301 for 2.0 miles to its intersection with U.S. Route 9. Turn left onto Route 9 and proceed north for 0.2 mile, then turn right onto a paved road at a brown sign for the "Hubbard Lodge." Bear left at the fork, continue past a house on the left, and park along the right side of the road.
Walk back along the paved road to a junction with a grassy road on the left. Turn left on the grassy road and, almost immediately, you’ll reach a gate. A triple-white blaze on the gate marks the start of the white-blazed School Mountain Road, and a triple-blue blaze marks the start of the blue-blazed Fahnestock Trail. Continue ahead on the road, which soon crosses two streams on wooden bridges.
In about half a mile, you’ll notice two stone pillars on the left. The road formerly crossed the stream here on a steel-plate bridge, but the bridge was washed out by Hurricane Irene in August 2011. Turn right, descend stone steps, and cross the stream on two steel I-beams.
Just beyond, the blue-blazed Fahnestock Trail turns sharply right, leaving School Mountain Road. Continue along the blue-blazed trail, which parallels the stream, following an old woods road which has narrowed to a footpath. In 0.2 mile, the woods road leaves the stream, and about half a mile from School Mountain Road, the Fahnestock Trail turns left, leaving the woods road, and begins a rather steep climb of Round Hill on switchbacks.
At the top of the steep climb, the trail reaches a limited west-facing viewpoint amid red cedars, with Bull Hill (Mt. Taurus) in the distance. The trail continues up the cedar-studded ridge of Round Hill, climbing gradually.
After following the ridge for about half a mile, the trail bears right, descends slightly into a shallow ravine, then climbs more steeply on a winding path. It levels off and soon reaches a southwest-facing viewpoint from a rock ledge to the right of the trail just below the summit of Round Hill. This is a good spot for a break.
After climbing a little more to reach an east-facing viewpoint over the hills of Fahnestock State Park, with a communications tower on the right, the trail descends rather steeply to a woods road in a valley. The trail turns right onto the woods road, briefly joining the green-blazed Round Hill Bypass Trail, and follows the road as it bends left and climbs over a rise, then descends gradually.
Continue on the Fahnestock Trail as it levels off, crosses a seasonally wet area, then climbs gradually. After a short, steep climb of a rock ledge, the trail passes a limited west-facing viewpoint through the trees and continues to climb steadily to the crest of another ridge, first rather steeply, then more gradually. There are no views from the wooded summit (the highest point on the hike; elevation 1,180 feet), marked by a large lichen-covered boulder to the right of the trail.
The trail now begins to descend, first very gradually, then more steeply. After crossing a stream and climbing over a low rise covered with mountain laurel, the trail continues to descend, soon reaching a junction with the yellow-blazed Perkins Trail. You’ve now gone a little more than halfway along the hike.
Turn left at this intersection, leaving the blue-blazed Fahnestock Trail, and follow the yellow-blazed Perkins Trail, which descends on an old woods road to cross a stream, then continues through an area with many stone walls. It bears left at a fork and continues to descend along a cascading stream, reaching its terminus on School Mountain Road. Turn right onto School Mountain Road, cross a stream on rocks, then immediately turn left onto the red-blazed East Mountain Loop, passing an abandoned farmhouse on the right.
Follow the red-blazed trail along a woods road bordered by stone walls. Soon, the road begins to descend. At the base of the descent, it crosses a stream on rocks in an area in which relics of the former agricultural use are abundant. The area is criss-crossed by a series of stone walls, and just before the stream crossing, the rusted iron wheels of an old farm wagon may be seen to the left of the trail.
The road now begins to climb, passing a stone foundation on the left. Near the top of the rise, follow the red-blazed trail as it turns left, leaving the woods road, and begins a steady ascent of the ridge of East Mountain. After bearing left at the crest of the rise, the trail continues along the summit ridge to reach a limited seasonal viewpoint through the trees just below the summit. The view is to the west and north over the Fishkill Ridge, with South Beacon Mountain (marked by a fire tower) and North Beacon Mountain (the site of several communications towers) directly ahead.
The red-blazed trail now begins a steady descent, with Round Hill (which you climbed earlier in the hike) visible through the trees on the left. On the way down, you’ll cross a number of stone walls and follow old woods roads for part of the way. At the base of the descent, you’ll cross a stream on a wooden footbridge and reach the end of the East Mountain Loop. Proceed ahead (southwest) on the white-blazed School Mountain Road, which immediately recrosses the stream on another wooden footbridge.
Follow School Mountain Road through a pleasant valley for about a quarter mile, paralleling a stone wall and a wide stream. After crossing a wooden bridge over a tributary stream, you’ll reach a junction where the yellow-blazed Hubbard Loop Trail begins on the right. Bear right and continue on the Hubbard Loop Trail, which climbs gradually on a woods road bordered on the left by a stone wall, passing abandoned farm settlements along the way.
Just beyond the crest of the rise, the trail bears left, leaving the woods road, then rejoins the road just ahead. The road is now bordered by stone walls on both sides. Soon, you’ll pass an interesting stone structure on the right.
After curving to the left, the Hubbard Loop Trail passes between two stone pillars and ends at School Mountain Road, opposite the steel I-beams that you used to cross the stream earlier in the hike. Turn right onto the white-blazed School Mountain Road (also the route of the blue-blazed Fahnestock Trail), retracing your steps back to the starting point of the hike.