Halloween Hikes in New York and New Jersey

Hiking in the fall is pretty much perfect: the air is crisp, the temps are cool, and the changing leaves offer spectacular views. This October, why not add a little Halloween spirit to your next outdoor adventure? From the Devil’s Path to Hell Hollow, we’ve rounded up some of the “spookiest” hiking spots in our region. Start planning your trip… if you dare.

Devil’s Path

Often cited as the toughest hiking trail in the East, this 24-mile path through the Catskills features 18,000 feet of elevation gain and loss. This section hike is a strenuous one-way route (requiring a shuttle) that traverses the four peaks on the eastern half of the Devil’s Path, climbing about 5,000 vertical feet. It may feel like a wicked haul, but it’s worth the effort, with amazing views of Platte Clove, Kaaterskill High Peak, and the Hudson River. Hike description.

Raven Rocks

Quote Poe while taking in the spectacular, unobstructed view on Raven Rocks on this loop hike through Westchester County’s Ward Pound Ridge Reservation. Hike description.

Jenny Jump Mountain

According to legend, Jenny Jump in Warren County, N.J., derives its name from Jenny Lee, who was accosted by (depending on the account) either a spurned suitor or a Native American on a remote area of the mountain. She was chased to the edge of the cliff and chose “death before dishonor,” jumping to her demise. Could her ghost be wandering these trails? You just might find out on this short loop hike through Jenny Jump State Forest, or on a longer loop that takes you on the ominously named Ghost Lake Trail. Both provide beautiful panoramas and views of interesting glacier erratics. Short loop description. 
Long loop description. 


Doodletown, a small, isolated community settled by loggers and miners in the 1760s in what is now Harriman State Park, got its name from the Dutch phrase Dood Tal for “dead valley.” Spookier still, today it’s a bona fide ghost town. There once was a church, a school, small businesses, two cemeteries, and 70 houses with 300 residents (at its peak in 1945). In the mid-1960s, the town was abandoned, and now only the cemeteries remain. Doodletown overview.  

Sleepy Hollow

Are you brave enough to explore the stomping grounds of the Headless Horseman? Two hikes through the town made famous by Washington Irving take you by the Sleepy Hollow Cemetery for extra chills. Hike 1 description.
Hike 2 description. 

Hell Hollow

Hell Hollow, located in the Fishkill Ridge Conservation Area in Dutchess County, N.Y., is reached after a brief rock scramble. It offers a view of the sheer vertical cliff on the other side of the notch; look down at your own risk! (But the views of the Hudson Valley are amazing.) The parking area for Fishkill Ridge is closed at Pocket Road and hiker parking is now only allowed on Main Street. Hike description. 

Hell Hole

Hell on earth is in Bear Mountain State Park… or at least Hell Hole is, anyway. The red-on-white-blazed Popolopen Gorge Trail runs past Hell Hole, a prominent waterfall in Popolopen Gorge. Hike description.

Witch’s Hole State Forest

The Witch’s Hole Conservation Area is a remote and spectacular part of Minnewaska State Park Preserve in Ulster County, N.Y. For a bewitching camping experience along the Long Path, pitch a tent in Witch’s Hole State Forest. Hike description.