Round Hill Loop
Directions to trailhead
From 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 -- the first, on a wooden bridge, and the second, on a steel-plate bridge..
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. Turn left onto the woods road, the route of the green-blazed Round Hill Bypass Trail. Follow this trail as it narrows to a footpath and continues a gradual descent, crossing several intermittent streams and stone walls on the way down.
In three-quarters of a mile, the trail reaches the base of the descent. The trail now bears right, climbs a little, and parallels a scenic stream on the left. Soon, the Round Hill Bypass Trail ends at a junction with the white-blazed School Mountain Road.
Turn left onto School Mountain Road, which immediately crosses the stream on a wooden footbridge. Continue along School Mountain Road for about a quarter mile, passing through a pleasant valley and paralleling a stone wall and a wide stream.
After crossing a steel-plate 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.