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Mythical Creature of Origin:
Popularized By:
“The Legend of Sleepy Hollow” by Washington Irving
Commonly Featured In:
Film, Television, Video Games

If ever there was a de-facto mascot towards the Halloween season, I’d honestly say that it was the Headless Horseman of Sleepy Hollow who only outranks Jack-o’-Lantern by a small margin simply for the fact that his tale is one that is easily the most recognized of Hallow’s Eve tales.

As stated above, the Headless Horseman was likely conceived by the notion of creatures from Irish myths and legends known as dullahans or “dark men” as their name translates. Contrary to what the name might imply, dullahan are in fact a type of fairy that resemble humans, most often men, who carry their head like a sack or hold it up.

They are said to wield a whip made from the spine of a human corpse and that should a dullahan stop its ceaseless ride if only for a moment, that means that a death is about to occur. Should a dullahan speak the name of someone though, that person is said to die right on the spot, more likely from fright than by anything from the dullahan itself.

As to the one made famous by Washington Irving’s classic tale “The Legend of Sleepy Hollow,” there’s a bit of a darker origin. For one thing, no matter what variations of the tale are done in film or television, the Headless Horseman was always at one point an ordinary, if not slightly extraordinary, mortal man. In the original tale itself, he was a Hessian artilleryman who was killed during the Battle of White Plains in 1776 by way being decapitated by an American cannonball.

The shattered remains of his head were left on the battlefield while his comrades hastily carried his body away and eventually had him buried in the cemetery of the Old Dutch Church of Sleepy Hollow. From then on, the Headless Horseman would arise every Halloween night as a malevolent ghost, furiously seeking his lost head.

His strength and prowess are variable by the telling of his tale but for the most part, the one true power behind the Headless Horseman is fear. For no matter how far we as a people have come since those times huddled in caves and grassy huts, the instinctual fear of flight from a predator is still pumping strongly in our veins. True, the Headless Horseman is but a man without a head but one who has nothing to lose and everything to gain in chasing down those who are still in possession of their own head and believe you me, there is nothing more dangerous than such an individual.

In more modern times, there have been many variations to the myth behind the Headless Horseman which include, but again is not limited to, being an incarnation of the Horseman of Death from the Four Riders of the Apocalypse, to being a bloodthirsty and outright monstrous individual whose head was cut off in retaliation for his crimes and buried separately from his body so that he may know no rest in the hereafter.

Even the game World of Warcraft has their own rendition of this classic tale and one that I’ll share via the video below simply for the length it goes and the visuals necessary to truly comprehend the horrible tragedy that is this particular Headless Horseman.

What is one important thing to note of the Headless Horseman however is the fact that he does bare some weaknesses much the same as most ghosts. He cannot enter holy ground nor can he cross running water, an often used symbol of cleansing one’s own soul. However, do not think yourself safe should you find yourself behind church walls or across the end of a bridge. For though the Headless Horseman cannot enter nor cross, he can still reach out and strike from afar if need be, often using the jack-o’-lantern replacement for his head as a burning missile of death and despair to his quarry.

So go out into this Hallowed night, you might find yourselves some delight, but take heed my words rhymed and true, you might find yourselves with more than you can chew.

For in this night unlike any other, there are monsters, ghosts, and all sorts of bother. So keep close to those you hold dear and listen well to your hearts’ whispering fear.

For you never know just when or where, monsters can come from here or perhaps just over there. Still, regardless of monstrous frights or sugary delights, I wish you all the most haunted of nights.

Happy Halloween.