Every October He Rides Again

The Headless Horseman has been riding longer than America has been alive. He thundered through Europe before the United States even existed, faceless and relentless, impossible to bury. In Germany he was the Wild Huntsman, storming through forests with his dogs. In Ireland he was the Dullahan, holding his own skull like a lantern and whispering names that doomed the listener to death. In Dutch folklore he was a cursed rider who could never stop. The ghost crossed the Atlantic tucked inside the memories of settlers and refused to stay quiet. Washington Irving did not invent him. He simply caught him and pinned him to the Hudson Valley like a butterfly specimen that keeps fluttering long after the pin is set.

That is the genius of “The Legend of Sleepy Hollow.” It is not fantasy but folklore curating itself into literature. Irving took a ghost that already existed and gave him a church, a bridge, a cemetery. He put coordinates on the haunting. That is why it feels so alive. Because you can go there. You can stand in Sleepy Hollow and realize you are in a place where myth has a street address.

The Old Dutch Church still stands, seventeenth-century timbers pressed against the centuries. The burying ground around it is crowded with stones carved with skulls and angels, a sculpture garden of death. Irving is buried there too, accessioned into his own legend, a man who understood that the best way to live forever is to write yourself into a ghost story and then lie down in the same soil. The entire town is the museum that keeps the Horseman alive.

He has been illustrated and reinvented again and again. Currier and Ives made him terrifying, a storm of hooves and shadow crashing over Ichabod Crane. Disney turned him into a cartoon nightmare, playful but still enough to scare children for life. Tim Burton dressed him in leather and fog and blood, a gothic daddy with no face. And now he lives in parades at Disney World, in haunted hayrides, in wax museums, in plastic skeleton displays at Target. He is folklore but he is also branding. He is both art and pop-up Halloween decor. He belongs to everyone and no one.

That is what makes him so erotic. He is faceless pursuit, stripped of shame, stripped of hesitation, stripped of humanity. A man with no head is a man who cannot explain himself, cannot lie, cannot ask for forgiveness. He can only chase. He can only want. He can only take. That is why he endures. Because he is every appetite compressed into a body that never stops moving.

The Horseman is funny in Irving’s version. Ichabod Crane is ridiculous, a lanky schoolteacher undone by his own superstition. But even then the laughter curdles. There is something too real about being chased out of town by a faceless rider. The story refuses to end cleanly. That is why it stuck. Folklore is like sex. It never stays neat. It spills, it gets retold, it turns into something different every time you touch it.

I spiral because the Horseman is everything at once. He is European revenant and American icon. He is high art and kitsch. He is comic and terrifying and hot. He is Rip Van Winkle’s brother in the sense that both stories tell us America was born haunted. Rip sleeps through a revolution. Ichabod is chased out of town by a headless ghost. Both men fail. The ghosts win.

Every October he rides again. In the cartoons, in the parades, in the cemetery, in the pop-up ads for haunted attractions. He cannot die. He is the boyfriend who never leaves. He is the faceless figure you see at the edge of the road when you drive home too late at night. He is folklore that insists on being retold, that insists on riding again, that insists on chasing you down.

And in my mind he always catches me. I hear the hooves closing in. I feel the air split open behind me. I feel his arms pulling me off the ground and onto the horse, strong and faceless, pressing me down. There are no words, no questions, no explanations. Just a body that refuses to stop. Just hunger. Just the rhythm of pursuit that does not end. That is the Horseman’s gift. He cannot finish his own story so he finishes mine. He proves that history is never clean, that folklore is always filthy, that America’s most enduring boyfriend is a ghost with no face.

The Headless Horseman is my favorite American boyfriend. And I hope he never stops riding. Because some nights when I am walking home and the street is empty and the air feels too sharp, I wonder if he is out there. Not just a story. Not just a folktale. Not just a cartoon or a parade float. Real. Waiting at the edge of the road. Ready to chase again.