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The Case of the Dark Man

Updated: Mar 10

Friends and Fellows,


I’d like to introduce to you my favorite scary story. The Headless Horseman is heralded as one of the U.S.A.’s first folk stories, but did you know it wasn’t invented there? The most well-known version of the story was originally a short story written by Washington Irving, called The Legend of Sleepy Hollow, which was written during an Irving family holiday in the UK. It stands to reason, then, that he would have been inspired by the Irish, Scottish, and other European “myths” of headless riders that date back to the middle ages or even earlier.


In Irish folklore, the horseman appears in three ways. As the Dullahan (the dark man) this demonic fairy carries his detached head under one arm and attacks with a whip made of human spine. If he calls your name, it’s already too late. As the Cóiste Bodhar, he is the headless driver of a black carriage of death. As Gan Ceann, the headless rider is scared off only by the presence of gold - which honestly just sounds like something rich people made up to scare poor people, but to each their own.


In Scottish history, the headless horseman was once human. He was decapitated in a clan battle on the Isle of Mull, thus denying him the chance to be chieftain.


In English writings, the headless horseman appears in the 14th-century work Sir Gawain and the Green Knight as the eponymous Green Knight. The knight is beheaded in his fight with our hero, and, picking up his severed head, challenges Sir Gawain to meet him again at his home in a year.

Far and away the most developed stories are those in the U.S.A. The story has been rewritten multiple times, appearing in Texas only forty years after Irving’s publication of Sleepy Hollow, mashed up with the rememberings of Creed Taylor, which were previously published as El Muerto. In this iteration, the horseman was a lieutenant in the Mexican army who shared military secrets and then deserted. He later was captured as a horse thief and beheaded. His captors strapped his headless body to a horse and sent them off across the plains.


The story of the headless horseman has also been turned into numerous films, including an animated version of Irving’s novel by Disney, a live-action tv show adaptation based on the same, and many others. My favorite anecdote is that it somehow also became a Soviet Cuban film in 1972. How I would love to get my hands on a copy of that movie.


Washington Irving’s headless horseman is still celebrated today in the village of Sleepy Hollow, near Tarrytown and White Plains, NY. And it is Irving’s story that prevails in all the history books if you go searching for information on the headless rider. Irving’s story itself is fairly simple, as all the best ghost stories are. Young schoolmaster Ichabod Crane is chased down a wooded road by a cloaked figure who carries their head on their side-saddle. Just as he is about to reach safety, Crane is hit by the thrown head, falls from his horse, and is never seen again. Although it is heavily rumored that Crane’s romantic rival was dressed up as the horseman and either chased him off or did away with him, most people will tell you that Crane was taken away to the spirit realm, and some will even claim to see his ghost in the area of his disappearance.


In modern depictions of the story, the headless horseman is depicted as a Hessian soldier in period clothing - cravat included - with no head, riding a dark horse. Rather than carrying his head at his side, he carries jack-o-lanterns, which he throws at people. And because he carries jack-o-lanterns, the headless horseman gets heavily associated with Halloween, which is fine by me since it is easily my favorite day of the year.


Additionally, I have had the pleasure of interviewing a number of people who have seen some version of the Headless horseman.


Jonathan Price reports seeing the ghostly figure in New York state the week before the annual festival held there in old North Tarrytown, renamed Sleepy Hollow after Irving’s book in 1996. Price had just arrived from New York City to visit his new girlfriend Abby at her family’s farm for fall break, and Abby wanted to give Price a tour of the local haunts before all of the tourists descended on the town for the festival. They walked through the Dutch Reformed church, across the Headless Horseman bridge, and had just finished inspecting the bronze statue of the rider in the town square when Price made his discovery. It was a clear, crisp autumn day, and a small cart had been set up to sell roasted nuts. As Abby was digging in her purse for her wallet, Price happened to glance up and over her head to see a rider headed down the road they had just come in from. Although riding away from town, the man was very clearly wearing hessian boots, a tailed coat, and a cravat, and had no head. He even carried a pumpkin under one arm. Price glanced back at the sculpture next to him to confirm what he was seeing, and when he turned back, the rider was gone. He tried to convince his girlfriend of this sighting, but she insisted he was making things up just to scare her, and that she didn’t actually expect him to believe the story, as it was, after all, just a legend. Although Mr. Price and his girlfriend had broken up by the time I [Agent Cook] interviewed him, he still recalled the events plain as day. Though he also claimed that he and Abby “drifted apart”, and that his sighting of this mythical being was “in no way responsible for the end of his relationship.” Being a bit of an expert on such things, it’s likely that he was lying about both.


Christopher Arnott reports seeing the headless rider from a distance near Lochbuie on the Isle of Mull one December, but his twin brother Hector, who was with him, says he didn’t see nothin’. Christopher insists the old clansman was riding across the snowy fields, the sun shining right through his ghostly visage. Hector says it couldn’tve been a ghost because they found hoofprints.


Debby Byrne of Adare, County Limerick, says the Cóiste Bodhar [Coist Boat-har] took her Mum away when she was young, and while her Da has always told her it was cancer, Debby says she saw the black carriage and its headless driver the night her Mum passed, and that the carriage is made of the most beautiful ebony and attended by two footmen, who assisted her mother’s ghost into the carriage before the vehicle rode off into the night. Her Da told her the next morning that her mum had passed, but Debby already knew.


Cassidy Erving reported seeing a headless rider near the property of Hermitage Castle when she was there for a ghost tour while on holiday. The rider was dressed in old tartans, carried no head, and rode in ever-growing circles as if searching for something.


While I have not had the pleasure of a sighting of any of the sources for this tale, I am what you would call an avid fan, and I particularly enjoy reading anything and everything about them that I can get my hands on.



Until next time,

Dr. Clark Cook





~Excerpt from Cook's Compendium Vol. XII


~Image Courtesy of b0jangles via Flickr under Creative Commons: https://www.flickr.com/photos/b0jangles/5132405446/


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