The familiar plot involves an itinerant teacher, [[MeaningfulName Ichabod Crane]], who takes up office in the school of the sleepy New York village of Tarrytown; the whole area, but particularly the nearby Sleepy Hollow, is supposedly haunted, especially by the figure of a headless [[strike:troper]] trooper on a phantom horse -- a haunting in which the superstitious Crane thoroughly believes.
Here Ichabod becomes a rival with the local hero, Abraham Van Brunt (better known by his nickname, "Brom Bones") for the affections of local coquette and heiress, [[PreppyName Katrina van Tassel]], who encourages the pedagogue, lest Brom think her love too easily secured. To that end she invites Crane to a "frolick" at her father's house, an occasion marked by the telling of ghost stories, particularly a tale by Brom of meeting the Headless Horseman, who vanished when they came to the brook by the Sleepy Hollow church.
When Crane departs for home on his borrowed horse, he is horrified to discover he is being shadowed by a cloaked figure on a horse -- whose head appears not to be on his head, but carried separately. The terrified Ichabod rides with the horseman in close pursuit, managing to cross the bridge, but when he looks back, the figure hurls its detached head.
The following morning, the schoolmaster has vanished, and hoof-prints and a shattered pumpkin at the bridge provide the only clue. Katrina marries Brom, who seems to know more than he tells about his rival's disappearance -- but though there are rumors that Crane had departed for another state, the old wives tell that he was carried off by the Headless Horseman. (An epilogue, not always reprinted, tells how the narrator [[BrokenAesop mocks]] a man who asked for the moral of the story.)