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Westchester offers a variety of hikes for all experience levels. Whether you’re an extreme hiker eager to test your skills or a family seeking a serene trail with water views, we have something for everyone. If you want to embrace Westchester’s spooky past while getting your steps in, here are three hikes that fit the bill. Just try not to get too spooked!
Rockefeller State Park
Sleepy Hollow
It’s no surprise that the spookiest town in Westchester County has a slew of dark history and folklore surrounding it. There are plenty of sites to explore throughout the village that offer walking tours, including The Spirits of Sleepy Hollow Country, Sleepy Hollow Cemetery Tours, Twilight Village at Sleepy Hollow located at Philipsburg Manor, and a handful of others. And while these tours and experiences dive into skin-crawling history and ghost stories, let us clue you in on additional local history that you can check out on your own time.
We talked with Emma Gencarelli, one of the authors who share ghost stories and local lore on sleepyhollowcountry.com, including articles on Raven Rock and Spook Rock. The first two hikes mentioned below are within Rockefeller State Park Preserve. The preserve boasts 1,800 acres of land, with the Rockefeller family donating over 1,771 acres to the State of New York beginning in 1983. Along the sprawling 45 miles of carriage roads decorated with stone bridges, creeks, and scenic greenery, it seems only right that there are a few ghost stories thrown in the mix.
Raven Rock
If you’re looking for a lengthy hike with rich history, Raven Rock is located on the eastern side of Buttermilk Hill about an hour into the woods.
The rock is supposedly haunted by three individuals. The first was a woman trekking in the woods attempting to avoid a hefty snowstorm. She found shelter from the storm and whistling winds within the ravine behind Raven Rock. Although the rock initially shielded her, she never awoke from her slumber behind the rock. It’s said that the spirit cries, which sounds like the screaming wind, warning others to stay away from the fatal spot. She is also known as The Wailing Woman of Raven Rock, per the late author of Chronicles of Tarrytown and Sleepy Hollow, Edgar Mayhew Bacon.
“It’s another one of those places in Sleepy Hollow Country whose presence still seems to cling to its legend even when it appears that those stories have long vanished from the land,” says Gencarelli.
The tale of two additional ghosts at Raven Rock have lesser-known details than the wailing woman. Bacon explains it as, “an Indian girl, who perished of a jealous lover, has an older claim; and the ravens used to tell of…a Colonial dame, who fled from the dreadful attentions of a too amorous Tory raider in the dark days of ‘The Old War.’”
Make sure you put on your hiking shoes and dress accordingly because Gencarelli notes that Raven Rock is not easy to get to. It takes about an hour from Buttermilk Hill Trail along the Old Orchard trail south towards Ferguson Lake and connecting to the Goat trail, from which you must walk another half mile down to finally hit the rock.
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The Spook Rock
If you set out in search of Spook Rock, it should be easy enough as the trail map marks its location, as well as other rock formations. The story that surrounds Spook Rock was passed down throughout history and survives as a solid story to tell around the campfire.
“Perhaps once, long ago, it was rooted in some semblance of truth, or perhaps none while some poor inhabitant of Sleepy Hollow tried to find a way to explain a weird feeling they had near a large, but generally plain and flat boulder they passed in the woods,” notes Gencarelli.
The story goes: a young Native American hunter stumbled upon celestial maidens singing and dancing on top of the large structure of Spook Rock, which at the time was a local meeting spot for the tribe. Once the maidens became aware of his presence, they scattered into the night. The hunter couldn’t get the maidens out of his head and routinely checked on the rock in hopes they would return. He eventually found them again on the rock in song and dance and married one of the celestial maidens, who seemed equally as enthralled by him.
The two had a child, but the celestial maiden longed for the stars and her friends who still sang on the rock. The desire to return to her friends became too strong, and she left the hunter and her child. The child couldn’t eat without its mother and eventually died. The hunter buried his son and headed off into the wilderness, from which he was never seen again. Later, the celestial maiden returned after what she thought was only a few hours but was actually a number of years to find their hut ruined and her family gone.
It’s said that on a clear night with a sky full of stars, you can see the lights dancing on Spook Rock. Or you may see the celestial maiden herself, walking through the forest in search of the family she lost.
Extra points for hikers who can find the bewitching chalk mural, which was done by a Sleepy Hollow artist.
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Irvington Woods
Within the Irvington Woods lies the only marked grave in the village. Hermit, or Johann Wilhelm Stolting, was born in Germany near the North Sea. It’s said that Hermit was a rather educated man, speaking German, Greek, French, and Hebrew, as well as a linguistic teacher and scientist. In his later days, Hermit found solace in creating buttons using a lathe he put together himself. The local legend would roam the streets and woods of Westchester and keep clean using the Saw Mill and Hudson Rivers. The quirky fellow even slept in a coffin he made of local chestnut wood. He became known as the Hermit of Irvington and passed in the village on January 10, 1888. His grave is marked on the Irvington Woods trail map, on the eastern side of the woods, so keep an eye out for it if you adventure out on a spooky hike this season.
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Related: Did You Know These 4 Famous Authors Lived in Westchester County?
