Are You Afraid of the Dark Wiki

The Headless Horseman is a character created by Tucker. He appeared in the episode "The Tale of the Midnight Ride".


The Headless Horseman was a Hessian soldier who fought and died in the American Revolutionary War. He died in battle when a stray cannonball shot his head off. Then night after night his evil ghost would ride through the woods of Sleepy Hollow searching for a victim to steal its head from to claim it as his new one. Why he chose to do this is unknown, and what kind of person he was before he died is unknown.

He became the rumor and legend of the town of Sleepy Hollow. Everyone was warned to be careful when heading for home late at night-time. One night, the town's new schoolmaster Ichabod Crane was very late heading for home. He was most unfortunate to take a wrong turn and he was right on Ichabod's trail. Ichabod tried to reach a holy bridge called "The Bridge of Souls, the one bridge he couldn't cross because he was pure and holy and if he did he would burst into flames and be defeated."

However Ichabod didn't make it in time and he hunted him down and threw an enchanted, flaming Jack-o'-lantern pumpkin at Ichabod and killed him.

Since then, every Hallowe'en in Sleepy Hollow, a curse of some sort caused the events of the night to take place all over again. He would reappear again riding through the woods searching for victims, and Ichabod Crane would still be looking for his safe way back home. When Ian Matthews and his friend Katie accidentally gave Ichabod Crane the correct instructions to the Bridge of Souls, Ichabod found his way back home. The story was then changed and altered and he never hunted down a victim, and still searched for one.

In Ichabod's place was Ian Matthews and Katie, and he immediately set his sights upon the both of them. The two of them realizes that they mistakenly changed the story and had to play it out and accidentally lead him to the Bridge of Souls.

He chased them riding on their bikes at full speed to the Bridge of Souls, but he anticipated them and went the other way. Katie then tried to divert his attention back over to Ian and she jumped in front of him. She was about to be decapitated by him when Ian called out to him. He ran up to him and Ian tried throwing his pumpkin at him, but it had no affect on him he just caught it with his cutlass.

Ian then waved to him taunting him and he chased him to the bridge. When he crossed the bridge, this caused him to burst into flames and vanish. However, he was soon shown to be alright and laughing, riding off in another part of the woods.

This was because Ian Matthews and Katie set the story back on the right track. Once again, he went back after Ichabod Crane and all the events that took place with Ian Matthews and Katie possibly ended up never happening.

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