Set in the small secluded valley of Sleepy Hollow, Irving’s short speculative story follows the rivalry between Ichabod Crane and Brom Van Brunt for Katrina Van Tassel’s hand in marriage. Mostly inhabited by descendants from Dutch settlers, the residents are known for their belief in superstitions and the supernatural, and have many stories to suffice their colorful imaginations. The story begins when the scrawny schoolmaster Ichabod Crane from Connecticut moves to Sleepy Hollow for a teaching job and rotates living with the families of his students. This type of living arrangement allows him to grow familiar with the stories circling the strange town. The most popular phenomena being that of the Headless Horseman, supposedly ghost of a Hessian soldier who lost his head during a battle in the American Revolutionary War.
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Other than being an intriguing story of greed, superstition and the supernatural, Irving also uses his main character Ichabod as a means of satire, mocking the seemingly refined culture of city dwellers. It is no coincidence that the educated Ichabod trades big city life for the small Sleepy Hollow, and is victim to the many pranks played on him. The Legend of Sleepy Hollow is one of the earliest samples of American fiction which has remained a classic and favorite among its readers.