“The Legend of Sleepy Hollow” has become a classic ghost story, but the Headless Horseman legend did not originate with Washington Irving. Versions of the Headless Horseman have existed since the Middle Ages. They have appeared in Grimm’s fairy tales, Dutch and Irish folklore, and 19th-century German literature. It is not known how Irving came to know the legend, but placing the figure in a Dutch community aligns with its cultural origins. Ultimately, the legend is designed to warn against otherness among these small, often ethnically defined villages. In this case, Ichabod, an outsider attempting to gain access by controlling the education of the local children and wishing to marry the most eligible maiden, is chased away by the last unsuccessful outsider, the Hessian Horseman.

Irving creates a parallel structure that adds tension to the story. Ichabod is, in many ways, the opposite of the Headless Horseman. Ichabod is physically awkward, unintimidating, and nonconfrontational. He is a poor rider, and his lack of horsemanship is one of the keys to his downfall. Brom Bones and the Headless Horseman are physically imposing and skilled riders. These details lend credence to one version of the story’s ending, which implies that the Headless Horseman who chased