Description of Place: A former strategic post between the American Colonists and the British Army in the Revolutionary War, Sleepy Hollow is a beautiful idyllic valley north of New York City. Very little has changed in the area over two hundred years, and much of the area is a preserved historic park. Many of the structures have remained 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 and 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 charging along the old road the river going back to the Eighteenth Century is perhaps as iconic to Halloween and paranormal folklore as the image of the witch of classical folklore or the image of the Grim Reaper from the Middle Ages. His exact description has varied over the years from a black cloaked 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. However, over the years, several people have reported seeing a headless figure near the grounds of Sleepy Hollow Cemetery close to where the earthly bones of Washington Irving rest, but are the locals imagining the iconic image of Irving's famous figure because of the setting. or has Irving himself managed to bring his famous literary character to life.

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 1799 in the aftermath of the age of witch trials. It is generally believed Irving modeled this obscure official into his Ichabod Crane, but this line of reasoning is not generally accepted. Rather than being chased from town, he married into a wealthy family of landowners and stayed in the area. His descendants being the modern Crane family.

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, 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 standing idly 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 being faked. On three occasions, the horseman has walked out into traffic near the Pocantico River Bridge and was deliberately hit. A few drivers have seriously searched for the cloaked figure if but to find empty space in the beams of their headlights and often grabbing a drink at the nearby bar to calm their spooked and frazzled nerves. As tradition goes, the bartender running the pub down the road has heard several drivers come in to regain their wits after thinking they have hit and killed a living person.

"The most recent case was just last December..." Nate Orwell, the owner and the proprietor of the Witch's Brew Bar and Grill off Broadway in Sleepy Hollow, told the CGS. "This salesman coming down from Albany came stumbling in looking for a phone to report hitting a figure standing in the highway that he couldn't find, but I sat him down, offered him a free drink and as he gripped the shot glass and composed himself, he described for me in detail on how he was surprised by this cloaked figure that seemed to vanish as he drove through it. Convinced and scared to death, he told me how he searched the road for what he had struck and finding nothing, he came here for help.

"Well, I calmed him down and told him the stories of the horseman over the years, but he never believed it, but as he perused the newspaper accounts going back to the Forties of this figure, you could see he was slowly starting to accept it. He was trying to stay as rational and as logical a person as possible as if he didn't want to believe in ghosts, but gradually he began to accept it... He had to confess that he had seen a ghost."

Although sightings are often few and far between, Orwell believes there are many more reports that don't get reported and are instead passed off as prowlers or sightings of black bears. Numerous homes in the vicinity of the old Revolutionary War battlegrounds have reported a figure in black lurking on their property and in addition to them, a few hunters have described the apparitions of figures in Colonial-era garb staggering and collapsing in the trees. Others have even reported hearing distant echoes of gunfire and cannons. 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.

"In my opinion," Orwell adds. "I think those kids were on something or dabbling in devil worship. The idea that the horseman wore a pumpkin on his stump is a modern notion that came with the commercialism of Halloween. The figure seen at the Crane Estate in 1976 was also described as wearing a jack o' lantern pumpkin head but that eventually turned out to be part of a financial scam."

Even today, Sheriff August Corbin gets annoyed by the police reports from people who describe seeing someone exploiting the legend by dressing in black, concealing their head and riding a spectral horse at full gallop along the highway for motorists if but to charge through the road and vanish into the woods. However, he's been to the area near Sleepy Hollow Cemetery several times, and while part of the time he can identify the Halloween hoaxers by the use of the horses and gear, but during the rest of the year, there is a remarkable absence of physical data.

"People can hear horses and hoof beats, but we never find their footprints." He adds. "The liars claim they hear roaring laughter and the sound of a cutlass scraping along their houses, but the real people are often too terrified to repeat what they saw. When I replaced Sheriff (Isaiah) Izzy Crockett in this job in 2000, he took me aside and over a bottle of Scotch described years of horseman sightings going back to the 1930s, including the arrested hoaxers from over the years to be wary of in the case. I take every sighting seriously, and I can tell in a few minutes if its going to be the real thing or a waste of my time. The fakes flare up every Halloween because of the book, but during the rest of the year, I hear anywhere from about seven to twelve cases of activity from the old battlefield and the cemetery along with the rare Sasquatch sighting." 

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. During the height of the American Revolutionary War, the surrounding area was the scene of marauders and infested with refugees from Europe. Westchester County was the site of many raids, skirmishes, war crimes, marauding and ravishing after the Continental Army abandoned it in October 1776. The British occupied the country south of the Bronx River, and the American lines were fortified north of Peekskill, leaving Westchester County as a thirty-mile stretch of scorched and desolated no-man's land, vulnerable to outlaws, raiders, and vigilantes. Besides droves of Loyalist rangers and British light infantry, Hessian Jägers, who were renowned as sharpshooters and horseman were among the raiders that often skirmished with patriot militias. After the war, the area became a small Dutch community under the jurisdiction of North Tarrytown, New York, which changed its name to Sleepy Hollow in 1997 to attract tourists and exploit the legends of the area. A statue of Ichabod Crane threatened by the Horseman was placed on Route 9. The local high school football team even calls themselves the Horsemen.

While it is believed that Irving based his story on actual local legends, historians believe the characters of Ichabod Crane and Katrina Van Tassel may have been based on local residents known to the author. The character of Katrina is thought to have been patterned upon Eleanor Van Tassel Brush, and named after Eleanor's aunt, Catriena Ecker Van Texel. Ichabod Crane himself was an Army Captain that Irving had encountered in Sackets Harbor, New York while serving as an aide-de-camp to New York Governor, Daniel D. Tompkins during an inspection tour of fortifications in 1814. He may have further patterned the character in after Jesse Merwin, a school master at the local schoolhouse in Kinderhook, further north along the Hudson River, where Irving spent several months in 1809.

Identity of Ghosts: Although fictionalized by Irving, the basis of the short story is based on the true story of an unidentified Hessian soldier who lost his life in combat. During the Revolutionary War, the British Army recruited many Hessian soldiers from Germany as mercenaries to storm the land and lay waste to the Colonist forces ahead of them. The Hessians were known to be brave bloodthirsty fighting soldiers trained specifically for war and extreme bloodshed, specifically in laying a siege ahead of the British Army to come in afterward and reap the benefits. One of the most bloodthirsty among the men lost his head in a cannon blast and died where he fell. Although the soldier in question was never named, this story was been passed down orally until Washington Irving published it as a part of fiction. Since the Early Nineteenth Century, this specter reportedly comes back looking for his head and continuing the bloodshed of his long-forgotten battle.

Most scholars however don't give the legends of the Hessian soldier much credence, pointing out that the Dutch settlers to the area most likely brought their legends with them. Stories of headless figures on horseback date back to the folk tales of the "Wild Huntsman" of Northern Europe, specifically Denmark, Germany, Ireland, Sweden and England.  

In 2008, parts of the area relevant to the horseman was investigated by the cast of "Most Haunted." They also featured several of the less prominent ghosts in the area such as a female apparition who attends a grave at Sleepy Hollow Cemetery and a sinister figure in black in the churchyard who is believed to also be the Horseman. A figure believed to be the historical Ichabod Crane wanders a local creek back and forth where a bridge once existed, quite possibly the actual bridge from the original story. Stories of phantom hoof beats are also sometimes heard in the area.

Source/Comments: Sleepy Hollow (2013)/ 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 Cemetery and Grounds in Sleepy Hollow, New York and upon other headless phantom cases, such as Lakey's Creek in McCleansboro, Illinois .

Updated: 10/09/2013