SLEEPY HOLLOW

Location: Sleepy Hollow is a small Dutch community located at North Tarrytown, New York and crossed by the Pocantico River in Westchester County.

Description of Place: Sleepy Hollow is a beautiful idyllic valley north of New York City. Very little has changed in the area over two hundred years. Many of the structures remain the same as they stood in the Eighteenth Century. The whole area is roughly bordered by the Hudson River to the west, Highway 100 running northeast north Tarrytown to the south. Washington Irving is buried in the local cemetery.

Ghostly Manifestations: The Headless Horseman is by far the most famous paranormal figure from American literature, but few realize that when Washington Irving wrote his famous short story that he was actually weaving a piece of fiction around an actual ghost story that really existed. The unearthly and spectral vision of a headless horseman has been seen charging along the river going back to the Eighteenth Century. His exact description has varied over the years from a black horseman waving a rapier atop a dark steed, to a headless skeleton on horseback and to a dark horseman with a jack o-lantern as a head.

While there is no clear evidence that figures named Ichabod Crane, Brom Bones or Katrina Van Tassel ever existed, there is an affluent family named Crane whose estate is situated north of Sleepy Hollow on the way toward Ossining and points north. They are not descendants of any spindly and skinny schoolmasters who were driven out of town, but rather the relatives of a New York constable named Isaac Crane who came to the area to investigate a series of forgotten grisly murders in the aftermath of the age of witch trials. It is believed Irving modeled this man into his Ichabod Crane. Rather than being chased from town, he married into a wealthy family of landowners and stayed in the area. 

Experiences concerning the horseman have been limited nearly entirely to the winter months when the fog rolls in land off the river. People in their homes have heard the sound of distant hoof beats charging down the main lane. No one has been reported as encountering and losing their head has ever been reported, but a few have said they have seen the horseman moving through the fog. During a Halloween party in 1976 given by heiress Beth Crane, as many as twenty people said they saw the headless horseman ride around the perimeter of the estate while others claimed to have seen him actually come to the house and stand outside a window. A Great Dane belonging to one of the guests actually bolted from the room sensing something paranormal about the decapitated visitor.

A miniscule number of drivers along Highway 100 have taken the time to report seeing the horseman just standing by the road, but the police have frequently discovered stuffed dummies and headless manikins made up to terrify drivers into causing accidents. This is not to suggest all the horseman’s appearances are fake. On three occasions, the horseman has walked out into traffic near the Pocantico River Bridge and was deliberately hit. A bartender running a pub down the road has heard several drivers come in to regain their wits after thinking they have hit and killed a living person.

As recent as 2004, the horseman has been seen galloping along the highway near the old cemetery. Described as a horseman with a pumpkin for a head, his specter was reportedly spurred into new activity by the arrival of Ian Cranston, one of the witnesses, who also claimed to be a descendant of the historical Ichabod (nee Isaac) Crane.

When he is not acting as a traffic hazard, the phantom has been seen lurking through the cemetery at dusk and at dawn when it is not quite as bright. In recent years, a group of people on a historical tour noticed the headless figure moving through the trees around them and commended their guide for heightening their experience with someone posing as the horseman.  Their guide merely chuckled nervously along with them because he had no idea who the figure was or wasn’t.  

History: Sleepy Hollow predates 1697 as a community. The site of numerous military skirmishes, most of them connected to the Revolutionary War, the small farming and historical community is still very nearly the same as it was when Washington Irving first documented the local ghost story.

While it is believed that Crane based his story on actual events, it has recently come to light that the Ichabod Crane he wrote about could not have been based on Isaac Crane. Beth Crane’s great-great-grandfather had actually arrived in the community in 1876; far too recent for Irving’s story. While the family name might have been a coincidence, the idea remains that the family is descended from the character in the short story.  

Identity of Ghosts: The story of the Headless Horseman

During the Revolutionary War, the British Army recruited many Hessian soldiers from Germany to storm the land and lay waste to the Colonist forces ahead of them. The Hessians were known to be brave bloodthirsty fighting mercenaries trained specifically for war. One of the most bloodthirsty among them lost his head by a cannon blast and died where he fell. His ghost reportedly comes back looking for his head and to take back as many modern colonists as he can.

Comments: The Legend of Sleepy Hollow (1980), Sleepy Hollow (1999), The Hollow (2004) and Scooby Doo, Where are You (Episode: The Headless Horseman of Halloween) Hauntings patterned upon the actual Sleepy Hollow and upon other headless phantom cases.