"The Legend of Sleepy Hollow" is set circa 1790 in the Dutch settlement of Tarry Town, New York, in a secluded glen called Sleepy Hollow. It tells the story of Ichabod Crane, a lean, lanky, and extremely superstitious schoolmaster from Connecticut, who competes with Abraham "Brom Bones" Van Brunt, the town rowdy, for the hand of 18-year-old Katrina Van Tassel, the daughter and sole child of a wealthy farmer. As Crane leaves a party, he is pursued by the Headless Horseman, who is supposedly the ghost of a Hessian trooper who had his head shot off by a stray cannonball during "some nameless battle" of the American Revolutionary War, and who "rides forth to the scene of battle in nightly quest of his head."

Also includes "Rip Van Winkle."