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In search of the best fall hikes in the Catskills, we let history be our guide on this trio of classic trails.

The crunch of leaves underfoot. A crisp breeze on a sun-soaked October Saturday. The combination of sweater weather and weekend hiking can’t be beat wherever leaves turn red and temperatures plummet, but for timeless trails that never get old, New York’s Catskill Mountains deliver hikes of truly historic proportions you can’t find anywhere else.

A day’s travel from New York and Boston, the Catskill Mountains were America’s first vacationland. Popularized by writers like James Fenimore Cooper and Washington Irving, these cloud-swept vistas attracted the likes of Mark Twain and the painters of the Hudson River School throughout the 19th century. City-dwellers in search of the cool country life would adjourn to grand hotels like the Catskill Mountain House and Overlook Mountain House, which loomed more than 1,500 feet above the Hudson Valley on mountain ledges. After a century, fires and fuel-powered travel would permanently shutter these sky-high retreats, but their footprints endure to this day as eminently explorable testaments to the region’s early role in shaping America’s relationship with its wilderness. Explore that heritage — and even more historic legacies — on these three classic hikes through America’s first wilderness.

Overlook Mountain Trail

4.6 miles

Extensive as they are ghostly, the remains of the Overlook Mountain House appear out of nowhere at mile 1.6 on the 4.6-mile out-and-back Overlook Mountain Trail. In fall, the abandoned hotel’s stark concrete walls contrast brilliantly with splashes of colorful foliage. Leave an hour to explore the ruins, but know the day has only just begun. Over the next 0.6 miles, gain 220 feet to reach the summit of 3,140-foot Overlook Mountain. Ascend the Fire Tower for camera-ready 360-degree views of the Catskills, Ashokan Reservoir, and the distant Hudson River. Start at Mead’s Meadow Parking Area near the town of Woodstock and tread carefully, as this part of the forest is a rattlesnake habitat.

North-South Lake/Escarpment Trail Loop

10.3 miles

Where the Catskill Mountain House once stood, all that remains is one of the most stunning views in the east. Those hills in the distance? Massachusetts’ Berkshires. (Save them for another weekend.) But while history might not be visible from this escarpment lookout, it’s present in full elsewhere on the 10.3-mile North-South Lake/Escarpment Trail Loop, where 19th century rock engravings abound, having been painstakingly cut by enthusiastic tourists into the oddly shaped rock formations that dot the mountainside. Reach the open field where the Catskill Mountain House once stood at mile 4.5 and you’ll know from the wide-open vista why the site was chosen for the hotel. But don’t give too much credit to 19th-century visitors: the spot was a favored Mohawk Indian summer campground long before history-minded hikers made it a must-see weekend spot.


Cairn Fields

1.5 miles

If you’re in search of something more ancient and mystery-shrouded than hotel ruins, take the 9-mile lollipop loop to 3,091-foot Ashokan High Point, where ancient stone cairns, believed to be 3,000 years old, can found in large groups along the Kanape Brook Trail. The stone piles are thought to have been used to mark underground watercourses and remained in use through colonial times. Search the woods on your left at mile 1.5 for the large field of over 25 cairns. On the way to the summit, snack on wild blueberries from bushes that line the trail and surrounding fields. Do it in fall, when foliage is less likely to obscure towering views of the Ashokan Reservoir, a melding of water, wind, and sky not to be missed in any season — or century.

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Related Links:

Great U.S. Places to Hike in Fall

Exploring Vermont’s Rural Heritage

Fall Outdoor Adventures: A Guide