Monster of the Week: The Headless Horseman of Sleepy Hollow

Are you…well, like me? Someone who not only has loved Halloween from a young age, but ghosts, spirits, and gothic fiction? Then you know that there’s only one monster I can possibly talk about today.

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I’m sure you’ve all heard the story: superstitious schoolteacher Ichabod Crane arrives in the quiet town of Sleepy Hollow in upstate New York, where one fateful night he is chased through the graveyard by the ghost of a soldier who had his head shot off by a cannonball. He rides on his horse, desperate to reach the covered bridge that legend says the horseman cannot cross. When he’s just about made it, he glances behind him in time to see the horseman lob his severed head (or a flaming pumpkin if you prefer the Disney version), striking Ichabod and sending him flying off his horse. The schoolteacher is never seen or heard from again.

This story got me hooked not only on Halloween but on what makes spooky stories “work.” The Legend of Sleepy Hollow is a definitive ghost story with an innocuous, almost mundane opening that slowly segues into something ominous and foreboding as more and more eerie things start to filter in, and eventually culminates in a “holy shit is this really happening?!?!” moment. Not only that, but after all is said and done, you’re left to question what *really* happened. The original story is told in such a way that the true fate of Ichabod Crane is subject to interpretation. Some people think the midnight chase was all a prank that scared him so bad he fled the town, never to return. Others think he may have been murdered by a rival, while still others, of course, believe the infernal Horseman got his quarry. There’s no clear answer, and in the end, isn’t not knowing the creepiest thing of all?

See also: Dullahan (Irish Mythos). Not a ghost, but a demonic fairy who rides with his head in his arms and carries a whip of a human spine. When he stops riding, he calls out a name and that person dies. It may be more badass than its American cousin, but for me, there will only ever be one.

Happy Halloween everybody! See you on the other side.