Irving didn’t invent Sleepy Hollow’s ghosts. He just picked the most famous one.
The Headless Horseman has crowded out everything else, but the country he rides through was thick with stories long before Washington Irving arrived. Some of them are still out there, attached to specific rocks and hollows in Rockefeller State Park Preserve — including Raven Rock, which Irving names in the story itself as the haunt of a woman in white heard shrieking before winter storms.
This evening goes looking for those first, and saves the Horseman for last.
The walk
You set off along a lamplit path toward the foundations of Rockwood Hall, the vanished William Rockefeller mansion whose grounds were laid out by Frederick Law Olmsted — the same hand that shaped Central Park. What remains is a stone terrace on a bluff, with the Hudson below, the Tappan Zee Bridge to the south, and on a clear night the Manhattan skyline beyond it.
It is, in daylight, one of the most beautiful places in Westchester. After dark, with a lantern and a storyteller, it becomes something else.
The program moves from the Preserve’s own lesser-known lore into “The Legend of Sleepy Hollow” itself — and to the real places behind it, most of which are within a few miles of where you’re standing. Then the evening closes the way it has to: with the Headless Horseman, mounted, coming out of the dark.
Your storyteller
The evening is performed by David Neilsen, a Tarrytown-based author and storyteller who has spent years telling this story on the ground that produced it — at Sleepy Hollow Cemetery, at Washington Irving’s Sunnyside, and at the Poe Cottage, along with the New York Botanical Garden and the Hudson River Museum.
His Legend isn’t a recitation. He performs the tale and then opens up the history beneath it: the real people, the real places, and how much of what Irving wrote came out of a few square miles of this valley. He also performs a one-man show as Major John André, the British spy captured up the road in Tarrytown — which is to say the local dead are his regular company.
Know before you go
- When: Select evenings from October 22 through November 1, 2026, beginning at 6:00 pm.
- Where: Rockwood Hall, Phelps Way, Pleasantville, NY 10570. Rockwood Hall is the section of the preserve west of Route 9, separate from the main Preserve entrance — see the note below.
- It’s a walk, in the dark, on park paths. Wear proper shoes and dress for a night by the river in late October.
- Getting there: This one is difficult without a car — unlike most events in our car-free guide, Rockwood Hall is not walkable from a Metro-North station.
Finding the entrance
Worth reading twice, because this catches people out. Rockefeller State Park Preserve has two separate sections divided by Route 9. The main entrance, visitor center, and Preserve office are at 125 Phelps Way, off Route 117 — and that is not where this event takes place. Rockwood Hall is the western section, reached from Route 9 (Broadway) closer to the river, with its own separate access and parking.
If you’ve only ever visited Swan Lake and the carriage roads, you have not been to Rockwood Hall. Allow extra time, and confirm the meeting point with the Preserve before setting out in the dark.
Tickets: Buy on Eventbrite · Preserve information: parks.ny.gov or 914-631-1470
The Horseman turns up in more than a dozen places across the season — see our guide to where to see the Headless Horseman. For everything else happening this autumn, see Halloween in Sleepy Hollow Country.
Sleepy Hollow Music Festival