Ichabod Crane is the schoolmaster in Sleepy Hollow, a town with supernatural occurrences. A local favorite is the tale of the Headless Horseman, the ghost of a mercenary who lost his head.
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Ichabod Crane wants to marry Katrina van Tassel, the flirtatious daughter of a wealthy landowner, but she has another option, Brom Bones. After receiving the brushoff from Katrina, Ichabod leaves a social gathering in an nervous state.
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After hearing many ghost stories at the party, Ichabod goes home during the witching hour. Over and over, he imagines a ghost or goblin in almost everything he sees. Finally, he sees the headless horseman.
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The Headless Horseman matches Crane's pace, and finally chases him. Ichabod tries to get away on a borrowed horse, to reach the bridge quickly.
Ichabod makes it to the bridge and turns to see if the Horseman will disappear. The Headless Horseman throws his "head" at Ichabod, who falls off his horse and passes out.
The next morning, the townspeople find Crane's hat and his few belongings, as well as a smashed pumpkin, by the bridge.