Headless Horseman: The Halloween Spirit


It comes back to life: Halloween is back! In the tradition of my favorite holiday, I would like to pay homage to one of the great demons of scary fiction … but which one? For those of us who live the Halloween lifestyle every day of the year, choosing a monster that particularly looks like Halloween is a daunting task. While any old boogeyman is perfectly acceptable at this time of day, I want to point out a horror that can only exist in the cold of an October night: an iconic creature of all that this spooky season stands for! Well, after a lot of digging and breaking coffins, I found my perfect Halloween monster: ladies and gentlemen, take off your tops (open to interpretation) for … The Headless Horseman!

Stories of headless ghosts on horseback existed long before Washington Irving’s seminal story, “The Legend of Sleepy Hollow”. In fact, they have been galloping since the Middle Ages. Irish mythology has the Dullahan, a decapitated horseman who rides a black steed, puts his own head under an arm, and uses a spinal cord as a whip (probably the most metallic phrase you’ll read today). “Sir Gwain and the Green Knight”, a 14th century Arthurian poem, also featured a man with an unadorned neck. And in Scottish folklore there’s Ewen the Headless, a specter that’s … well, you know.

As haunting as these legends are, the most direct inspiration for Washington Irving’s horseman was that of Sir Walter Scott. The hunt from 1796 itself a translation of the German poem “The Wild Huntsman” by Gottfried August Bürger, which was based on Norse mythology (and I thought Bing Crosby made it all up). According to Irving expert Elizabeth Bradley, “Irving had just met and befriended Scott in 1817, so it is very likely that he was influenced by the work of his new mentor.” The historian says the poem is about “a wicked hunter who is doomed to be cast out forever by the devil and the ‘hellhounds’ as punishment for his crimes.”

Despite its obvious European roots, “The Legend of Sleepy Hollow” is as American as MAG Magazine. The 1820 short story, which first appeared in Irving’s collection titled Geoffrey Crayon’s sketchbook, Ghent., is perhaps the first true horror story to come out of the United States, and certainly one of the most famous. Set in the Dutch colony of Tarry Town (historic Tarrytown, New York) and incorporating historical details from the Revolutionary War, “Sleepy Hollow” brought ghosts to American literature. And while the Horseman hails from Germany to his fictional kingdom, I like to think of the Nogginless Nightmare as America’s first great bogeyman.


In Irving’s story, the Headless Horseman is believed to be the ghost of a Hessian soldier whose head was blown off by a stray cannonball during “an unnamed battle” of the Revolutionary War. The main haunting in Irving’s tale involves a gangly and superstitious schoolmaster by the name of Ichabod Crane. After a harvest party and a few ghost stories, Crane is threatened by the legendary ghost with his head on his saddle instead of the more fashionable shoulders. The Horseman pursues Crane until the schoolmaster crosses the bridge adjacent to the Old Dutch Burying Ground, where our dear Cavalier is said to “disappear, by rule, in a flash of fire and brimstone” while crossing him. . But, being rather cunning for a headless gentleman, our Cavalier points his head at poor Ichabod, sending the schoolmaster tumbling into the dust.

The next morning, old Ichabod is nowhere to be found, as if he had disappeared from the face of the earth. Of the old schoolmaster’s horrible ride, only a stray horse, a trampled saddle, an abandoned hat … and a broken pumpkin remain. Now, it is strongly implied that the “ghost” was actually just Ichabod’s romantic rival, Brom Bones, and that that fateful night of dread was just a run-of-the-mill farce, completely devoid of strangeness. However, the story is ambiguous enough that one might believe that Crane was “bewitched by supernatural means”. And that’s what I choose to believe, dear readers!

The power of the Cavalier extends far beyond the printed page. North Tarrytown, the town that inspired the legend, officially became Sleepy Hollow in 1996. Washington Irving, who lived in Tarrytown, is now buried in Sleepy Hollow Cemetery. Their high school football team is the Horsemen, and there’s even a monument dedicated to Ol ‘Headless. If there really is a real Halloween town, it’s Sleepy Hollow.


Since the silent era, hundreds of movies and shows have featured Irving’s Specter, the first being a 1922 image starring Will Rogers. Perhaps the most beloved of these cinematic takes is “The Adventures of Ichabod and Mr. Toad” from 1949, an animated feature film that combines “The Legend of Sleepy Hollow” with a narration of “The Wind in the Winds”. willows “. While we’re not without options, the Disney adaptation is my pick for the best. It combines burlesque and fear in a way that can only be achieved through animation. Another notable take is that of Tim Burton Sleeping Hollow, a free adaptation of the story. He owes much more to Hammer than to Irving, but it’s a perfectly weird yelp. And while Burton’s film reinvents the tale into a supernatural thriller, it retains the essential elements of the Legend. There was also a Sleeping Hollow TV series from 2013 to 2017, but I can’t imagine a show that ran for four years to be particularly true to a twenty-four page story.

The aforementioned broken pumpkin is a curious aspect of the horseman. What was once a clue to the spurious nature of the mind has become part of its mystique. No longer a quack’s tool, he has become the weapon of one of horror’s most revered villains. Over the years, the pumpkin has evolved into a substitute head, which I find much more original than a detached head. This pumpkin noggin is what separates our rider from the rest. This raised him above the average for appearances. This is the reason why he is the chosen monster for Halloween. May the Horseman ride forever!

About Norma Wade

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