Walk Sleepy Hollow's most haunted locations. 22 stops, self-guided. 3 stops free. No guide, no schedule — just you and the dark.
The Headless Horseman is just the beginning. A Hessian soldier lost his head to a cannonball near the bridge in 1776, and witnesses have reported a mounted figure in Revolutionary War uniform ever since. British spy Major John André was hanged at Patriot's Park after Benedict Arnold's treason plot collapsed — his ghost appears in full uniform, silent and watching. Washington Irving died at Sunnyside in 1859, and staff report his books flying from shelves on their own. This self-guided tour covers 13 free stops across Sleepy Hollow and Tarrytown, from the Old Dutch Church built in 1685 to Lyndhurst Mansion, where the original owner's daughter died at 19 under circumstances never fully explained.
On a dark autumn night in 1790, schoolmaster Ichabod Crane rode his borrowed horse Gunpowder along this very road, the trees closing in like skeletal ...
The Hessian soldier's decapitated corpse was found near this bridge in 1776, his head never recovered. Witnesses describe a figure in Revolutionary Wa...
Washington Irving purchased this Hudson River cottage in 1835, transforming it into an eccentric masterpiece of Dutch Colonial and Gothic Revival arch...
Washington Irving died in this house at age 76, allegedly of a heart attack—but some believe he was working on one final, terrifying tale. Staff repor...
The daughter of the original owner died at age 19 under mysterious circumstances—possibly suicide, possibly murder. Her ghost has been seen in the Ros...
This Gothic Revival castle was built in 1838 from limestone quarried by Sing Sing prisoners — men who died in chains just miles up the river. Its most...
Kykuit — Dutch for lookout — sits on the highest point in Pocantico Hills, and for four generations of Rockefellers, it watched over an empire. John D...
Major André cooperated fully with his captors, believing his gentlemanly conduct would spare him the noose. It didn't. His ghost appears in full Briti...
John D. Rockefeller Jr. spent his final years obsessing over the perfection of Kykuit's gardens. His ghost is seen pruning roses that no longer exist,...
This burial ground predates the American Revolution, with graves dating to the late 1600s when Dutch Reformed settlers first broke ground beside the P...
On September 23, 1780, three American militiamen stopped a man in civilian clothes near this spot along the Albany Post Road. The man identified himse...
A lighthouse keeper named Samuel Weston fell to his death in 1921 under mysterious circumstances. His final log entry read: "They want the light out. ...
Built in 1885 by chocolate magnate William Wallace, the Tarrytown Music Hall is the oldest operating theater in Westchester County. Its Queen Anne-sty...
The Armour family fled in the middle of the night in 1863, leaving all possessions behind. A maid's diary discovered in 2003 describes "the thing in t...
Catherine Vale's death was ruled suicide despite evidence suggesting otherwise—defensive wounds, a locked room, her diary missing pages. Her ghost app...
The Warner Library has served the Tarrytown community since 1929, but the land it occupies carries far older memories. The building sits along North B...
The woods surrounding Philipsburg Manor have been considered cursed ground since before the English-speaking world had a name for Sleepy Hollow. The W...
The Old Burying Ground contains victims of the 1776 typhoid epidemic, buried in mass graves with minimal ceremony. Paranormal investigators recorded 4...
The Sleepy Hollow ghost tour includes 22 documented haunted locations.
The first 3 stops are completely free — no account required. To unlock all 22 stops, a History Nearby premium subscription is $4.99/month or $49.99/year.
No. This is a self-guided walking tour. Each stop includes the address, a map pin, and the full haunting story. Walk at your own pace, start anytime, and take any route you like.
Plan for approximately 4.5 hours. This accounts for walking between stops and reading each haunting story. You can also split it across multiple evenings.
The most visited stop on our Sleepy Hollow tour is Headless Horseman Bridge at Route 9, near Patriot Park, Sleepy Hollow, NY 10591.
3 stops free in Sleepy Hollow. No guide, no schedule — walk at your own pace after dark.
Last updated February 22, 2026. Researched by the History Nearby editorial team.