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Total loop length = 6.0 miles
Summit Only Via Devils Path = 3.3 miles One Way
Elevation gain = 1,700’
Start at the trailhead and follow the Red Markers (Devils Path) for 0.5 of a mile and only 150’ of elevation gain to the intersection with Jimmy Dolan Notch Trail, Blue Markers. Stay left on the Devils Path for 1.25 miles to the intersection with the trail coming in on the left from Overlook Mountain. Continue ahead, for about 250 feet, follow the red blazes as the trail turns right, leaving the woods road, and begins to climb Indian Head Mountain. The trail climbs 1,300 feet in the next 1.6 miles, with steep pitches. After passing some overhanging rock, the trail turns sharply left and begins to head southeast. It soon reaches Sherman’s Lookout – a north-facing rock ledge just to the left of the trail, with awesome views to the north and east. North is Kaaterskill High Peak and Round Top, with Plattekill Mountain to the east. Continue ahead on the Devil’s Path, which now goes through a deep spruce-fir forest, with the trail often tunneling through the thick evergreens. The trail now descends for a short distance, then climbs very steeply up a rock crevice. At the top of the climb, turn right to reach an overhanging rock ledge with more views. The mountain directly ahead of you is the eastern peak of Indian Head Mountain, which you circled on the way up.
Continue ahead to another steep climb up a rock face (class 2 portion). Continue ahead a short distance to the summit, like many peaks in the Catskills the summit can be hard to find. Continue West while descending about 0.2 of a mile and 400 feet of elevation, you’ll reach Jimmy Dolan Notch – the low point between Indian Head and Twin Mountains. Turn right here and follow the blue-blazed Jimmy Dolan Notch Trail downhill. In 1.2 miles, the trail turns right onto a old woods road, which it follows across a stream to end at a junction with the red-blazed Devil’s Path. Proceed ahead on Devils Path for half a mile to the Trailhead.
Nothing special needed in the dry months.
Crampons for the winter months
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