Length: 6 miles • Elevation: 3,573 feet • Highlight: 150 year-old hemlock trees
Widely regarded as the toughest hiking trail in the eastern U.S., the Devil’s Path is more than 24 miles in length and crosses five of the Catskill’s 35 High Peaks — Indian Head, Twin, Sugarloaf, Plateau, and Hunter mountains (as well as West Kill). Infamous for its steep ascents (which often require both hands and feet to navigate), rocky footing, and false peaks, this is not a trail for the timid — or, for that matter, those with a fear of heights.
The Devil’s Path can be utilized as part of a day hike that takes you up and over any one of the six mountains it traverses. One popular but rugged route, the Indian Head Loop, follows the Devil’s Path to the Jimmy Dolan Notch Trail, which takes hikers into the notch itself — a V-shape carved into the rock that offers spectacular views of the Esopus Valley and the southern Catskills. On the descent from the summit, watch for the eastern overlook, which offers a 180-degree vista that takes in everything from the Ashokan Reservoir to the Berkshires (but watch your step: with a sharp drop-off of 3,200 feet, you wouldn’t want to lose your footing). Hemlock trees were nearly wiped out in the 19th century, when their bark was used by dozens of leather tanneries in the area. At about 30 inches in diameter, a number of the trees along this route probably date to about 1860.