“He still rides, they say, in the dead of night, seeking his lost head.”
With his hooves echoing in the darkness of the night and his evil laughter piercing even the earth, one knows that death is near. Everyone will have heard of the infamous Headless Horseman at least once in their life—but where does this legend come from and, more importantly, does it really exist?
American writer Washington Irving wrote and published what would become one of the first American ghost stories in a collection of 34 essays and short stories titled The Sketch Book, in 1820, under the pseudonym Geoffrey Crayon. A tale that has been written and rewritten over the years and which everyone certainly knows as The Legend of Sleepy Hollow.
Before we delve into the story properly, though, let’s take a few miles from the still-existing little town, because, strange as it may seem, almost every continent has its share of headless creatures, and an exorbitant number of them are curiously on horseback. Washington Irving may not have invented the story himself; in fact, there are numerous tales of headless knights that can be traced back to the Middle Ages, and it is almost certain that he was influenced by these stories. A prime example is the 14th-century Arthurian poem that narrates Sir Gawain and the Green Knight. The poem talks about one of the cavaliers at King Arthur’s Round Table as the main protagonist, challenged to a duel by a mysterious man—the Green Knight. However, the encounter turns into something unusual when the stranger reveals that he will allow Sir Gawain to strike once and only once and that he will return the exact same blow a year and a day later. The King’s cavalier accepts the offer and with one blow of his axe decapitates the man, who, however, does not drop dead. The Green Knight picks up the head and, as promised, returns after twelve full moons. Other representations can be found in India or in the long list of tales of the Brothers Grimm, where the figure of a headless man is depicted in a more heroic light. One of the most intriguing accounts of this singular figure, however, comes from Irish mythology, with a dark fairy called Dullahan (also known as Durahan or Gan Ceann)—strikingly similar to the spirit in Washington Irving’s collection. This morbid spectre rides through the nights of Irish festivals with a tattered dark cloak and a powerful black stallion, galloping wildly across the Irish moors and choosing his next victim. In his hands is a human spine and his snarling, rotting head, which he lifts so high into the sky that his eyes can devour every mile and every soul that approaches. Once it stops, however, it is time to shake in your boots because if the Durahan utters a name, all you can do is pray it is not yours. In some stories, he drives a black chariot, called a cóiste bodhar (coach-a-bower), made of bones and human skin, and in others, the horses are depicted as headless, as well. No locked door can stop the Dullahan, but it is said that he can be kept at bay when a golden object is thrown in his path.
Plenty are the similarities and differences with the ghost that haunts Sleepy Hollow, but Washington Irving’s tale stands on its own because it focuses on schoolmaster Ichabod Crane and his courting of Katrina Van Tassel, a young heiress also pursued by another important character—Brom Bones. The story tells that, after being rejected by Katrina at a party on the Van Tassel farm, the protagonist is chased by a headless horseman who hurls his head at the man, knocking him off his horse. The story ends with Ichabod never being seen ever again.
Oddly enough, almost everything the author wrote is grounded in reality. Irving, in fact, after fleeing New York because of a yellow fever epidemic in 1798, headed for Tarrytown, where, just across the river, lies the real Sleepy Hollow. Its cemetery also contains many of the names that inspired some of the characters, but it is the story of the Headless Horseman that is the most fascinating one. Although the famous wooden bridge where the chasing happened is not the same as it was two hundred years ago, the church and the hollow described in the most crucial part of the legend are very much real. What we do know is that Katerina Van Tassel did exist, but the evidence points more to her granddaughter, a persona more suited to the age of the character. In the creation of Brom Bones, instead, Irvin was influenced by two real and different people. The first was Abraham Martling, a war veteran who played a crucial role in organising Tarrytown’s defences during the revolution. The second was Abram Van Alstyne, a young man who played a trick on schoolmaster Jesse Merwin, persuading him to marry his fiancée, Jane Van Dyke. It is said that, exactly like in the legend, one night, after leaving Jane’s house, Jesse Merwin found himself followed by a ghostly knight wrapped in sheets. Jesse, although frightened, took the hint, proposed, got married, and supposedly was the man behind Ichabod Crane.
For the Headless Horseman, apart from Abram Van Alstyne, the author might have been influenced by a real Hessian soldier who was decapitated by a cannonball during the Battle of White Plains around Halloween 1776. Legends tell that an American lieutenant was in command and managed to kill the Hessian soldier with one brutal shot, ending the attack right there and then. What is interesting is that the Van Tassels may actually have connections with the Hessian soldier. It is said that, amid the British and American offensive, the family lost sight of one of their children, and only thanks to a Hessian enemy did they find the child. After the cannon tragedy, however, the Van Tassel family was supposedly so grateful for the help that they insisted on giving the man a proper burial, in case he was their magnanimous soldier.
And from then on… the rest is history.
It is entirely possible that Washington Irving did not craft the tale from his imagination.
But who knows?
Perhaps the Van Tassels truly did lay an enemy to rest in the old Dutch cemetery of Sleepy Hollow. Perhaps the legend is true. And perhaps, even now, the Headless Horseman rises in the dead of night—haunting the darkness, seeking revenge, stealing souls, and endlessly searching for his lost head.
Up, Off with his Head Illustration by my amazing twin Soul
Sources:
Did the Dullahan, the Irish Headless Horseman, Really Inspire ‘The Legend of Sleepy Hollow’?
The Old Dutch Church and the Headless Horseman: Separating Fact from Fiction
The Library of the Unseen 
Beautiful description of my sign! Thank you ☺️ 😘😘