The frightening gothic tale "The Legend of Sleepy Hollow" by Washington Irving climaxes with an exciting chase as Ichabod Crane attempts to flee from the terrifying Headless Horseman. However, it begins innocuously with a description of Sleepy Hollow, although there are forebodings of ghostly happenings in the area, and of Crane, the main character.

As Irving explains, Ichabod Crane has come to Sleepy Hollow to be the schoolmaster, "for the purpose of instructing the children of the vicinity." He is from Connecticut, which the author states is known for sending forth "country schoolmasters." Crane teaches all the children of the area in a one-room schoolhouse.

Irving explains that as schoolmaster, Crane is "a man of some importance in the female circle." He spends long evenings with the wives, listening to "marvelous tales of ghosts and goblins" and haunted places. These stories, especially of the Headless Horseman, would greatly disturb him later.

During the town's social events, Crane gets to know an eighteen-year-old girl named Katrina Van Tassel, the daughter of a wealthy local farmer and one of Crane's music students. What he comes to want after he arrives in Tarry Town is to marry Katrina. He imagines Katrina inheriting her father's farm and he and Katrina with "a whole family of children." They would then set out in a wagon for Kentucky, Tennessee, or some other place. This is his ongoing fantasy, but his challenge is that there are other suitors also vying for Katrina's hand.