The Headless Horseman, of course, is a major character in “The Legend of Sleepy Hollow.” But the ghostly rider—and, especially, his head—also symbolize the tension between reality and imagination, between the natural and the supernatural, held by many of the townspeople. The Horseman is fixed in historical fact: there were, indeed, many Germans or “Hessians” hired by the British to fight against the American army during the Revolutionary War. Indeed, though the townspeople’s stories about the Galloping Hessian may be ghost stories, it hasn’t been long since a real Hessian rider (one alive and with a head) could provoke fear in them for good reason—as the enemy. By becoming headless, the horseman can become nestled within society’s cultural and imaginative traditions, even while remaining based in history.
But in other ways, the horseman symbolizes Ichabod’s less defensible inability to separate fiction and fact. Indeed, it loses its head just as Ichabod, more metaphorically, loses his each time he returns home spooked by the Dutch ghost stories. Brom Bones takes advantage of this lack of reason. Brom uses his head—both intellectually in plotting and strategizing, and practically in hurling a “head” at Ichabod.