The story is set in the 1790's in the Dutch settlement of TarryTown, NY, in a secluded glen called Sleepy Hollow. Ichabod Crane, the protagonist, is a stern schoolteacher and singing instructor who has come to Sleepy Hollow, New York, from Connecticut. He falls for one of his singing students, Katrina Van Tassel, an eighteen-year-old known for her beauty and her wealth.
Among Ichabod's rivals, Brom Bones is his greatest threat. Brom is a rowdy and boisterous troublemaker, known throughout the country for his heroics and feats of strength. He is liked and respected by almost all.
At a party at the Van Tassel's farm men start telling stories and Brom Bones tells a story of the time he encountered the Headless Horseman and offered to race him for a bowl of punch.

As Crane leaves a party , he is pursued by the Headless Horseman, who is supposedly the ghost of a Hessian trooper who had his head shot off by a stray cannonball during "some nameless battle" of the American Revolutionary War, and who "rides forth to the scene of battle in nightly quest of his head". Ichabod mysteriously disappears from town, leaving Katrina to marry Brom Bones, who was "to look exceedingly knowing whenever the story of Ichabod was related". Although the nature of the Headless Horseman is left open to interpretation, the story implies that the Horseman was really Brom Bones in disguise.

North Tarrytown, changed it's name to Sleppy Hollow 1996.

See:
YouTube - headless horseman

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