Headless Horseman!

The headless horseman has appeared in many forms of literature throughout history and throughout the world. Many countries have their own unique version of the legend in which some form of the headless horseman appears. In the United States, various states have their own version of a headless horseman tale; Texas' version of the legend, written by Thomas Mayne Reid in 1865 or 1866, tells of ghosts of beheaded horse thieves, who roam the countryside.

The more noted and recognizable headless horseman of today imitates the one that appears in Washington Irving's short story, which was published in 1820. The story is set in America, within a 1790's Dutch settlement that residents nicknamed “Sleepy Hollow”. Its protagonist is a schoolteacher named Ichabod Crane, whose apparent demise results from a meeting with the horseman. The horseman himself is allegedly a Hessian soldier from the Revolutionary War who was decapitated by a cannonball and now roams Sleepy Hollow on the back of his horse, with his severed head resting upon the pommel of his saddle. He is therefore also called the 'Galloping Hessian'. The Horseman is said to be incapable of crossing the covered bridge at the town entrance (a possible reference to the belief that ghosts cannot cross water), although he is shown throwing his head across a river to strike down Ichabod Crane. Ichabod's fate is left ambiguous; some of the background characters allege that he has been "carried off" by the Horseman, while others suggest that he has been frightened out of the county by the ghost and by the prospect of facing his landlord, later to become a lawyer in Philadelphia. It is implied later that the Horseman was in fact Brom Bones, Ichabod's rival for the hand in marriage of the local beauty Katrina van Tassel, who imitated the legend of the Galloping Hessian on purpose to kill or frighten away his competitor. The fact that a shattered pumpkin is found beside Ichabod's abandoned hat supports this, in that the pumpkin may easily have been used to simulate the Horseman's severed head. Intriguingly, there is no mention of a severed head in the story heard by Ichabod, though it is prominent in his own encounter with the horseman.

The legend of the Headless Horseman begins in Sleepy Hollow, New York. The Horseman was a Hessian of unknown rank; one of many such hired to suppress the American Revolutionary War. During the war, the Horseman was one of 548 Hessians killed in a battle for Chatterton Hill, wherein his head was severed by a cannonball. He was buried in a graveyard outside a church. Thereafter he appears as a ghost, who presents to nightly travelers an actual danger (rather than the largely harmless fright produced by the majority of ghosts), presumably of decapitation

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• A version referred to as a "darklord" appears in the Ravenloft campaign setting for the Dungeons & Dragons roleplaying game; it overlays itself on random stretches of barren road and hunts for lone travelers with the assistance of several of the heads of previous victims.
• In A Hollow Sleep by Chris Ebert, the Horseman is given an identity of "Heinrich Luneberg" and his origins are explored. The story is told from his perspective.
• In the Beetleborgs Metallix episode "Headless Over Heels," the Headless Horseman accuses Wolfgang of stealing his head. When he arrives in Charterville looking for his head, he attempts to find it or take one of the other monsters' heads in exchange. It is revealed that Little Ghoul had his head, and was using it as a bowling ball. Upon its return, bolts were attached to the head to keep it from falling off again.
• Dark Shadows (1966)