In "The Legend of Sleepy Hollow," what might the headless horseman symbolize?
The Headless Horseman could possibly symbolize the exotic strangeness and superstition at the heart of rural life. Ichabod Crane, though not originally a rural-dweller, is nonetheless wracked with superstition. He's obsessed with the supernatural, avidly devouring Cotton Mather's History of New England Witchcraft. And having deeply breathed in the local "atmosphere of dreams and fancies infecting all the land," Ichabod's already overheated imagination is now at boiling point. All of this adds to a chronic inability to distinguish fact from fiction.
The ending of The Legend Of Sleepy Hollow is famously ambiguous. We are not entirely sure, for example, that Ichabod actually perishes after his chilling encounter with the Headless Horseman. An old farmer just back from New York certainly doesn't think so. But perhaps Ichabod really did escape. Then we might venture to suggest that he didn't just flee from the evil clutches of the Headless Horseman, but also finally escaped the crippling superstition that held him and the rest of Sleepy Hollow in its grasp.
On this reading Ichabod's feverish ride of Gunpowder comes to look more like an act of heroism than of cowardice. In leaving Sleepy Hollow behind, Ichabod Crane has regained his life, one no longer marred by a debilitating taste for the weird and supernatural. Whether or not he's become a Justice of the Ten Pound Court, if he really has escaped then he's finally become his own man, a free individual no longer encumbered by myths and legends and all manner of strangeness.
One of the themes of American Literature and American folklore is the differences and comparisons of city people and country people. Ichabod Crane is a city man, educated , intelligent, gentile, but not the outdoor type. Once he falls in love with Katrina Van Tassel, he is in direct competition for her affection with Brom Bones who is a country man, a strong, skilled horseman, with a sense of humor.
When the headless horseman is seen by Ichabod Crane, it is done to prove to him that he does not belong in the country. He is weak, frightened and gullible.
The story behind the headless horseman about a Hessian soldier who lost his head during the Revolutionary War, and every night he rides his horse looking for his head, has made a distinct impression on Crane, who is interested in spirits and magic.
Brom Bones shows Crane that he is less of a man than he is, because he falls for the tale of the headless horseman and is scared out of his mind. He does not have what it takes to live in the country.
"Suddenly, he sees a large shadowy figure on the road ahead. It appears to be a headless man riding a horse, and Crane can just make out the shape of a head resting on the pommel of the saddle. Terrified, he races away, chased by the headless horseman. He is unable to escape. The last thing he remembers is the sight of the rider about to throw the head at him; struck by the flying object, he is knocked unconscious to the ground."