Along with "Rip Van Winkle", "The Legend of Sleepy Hollow" is among the earliest examples of American fiction with enduring popularity, especially because of a character known as the Headless Horseman believed to be a Hessian soldier who was decapitated by a cannonball in battle.

"The Legend of Sleepy Hollow" relates the tale 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 wealthy farmer Baltus Van Tassel. Ichabod Crane, a Yankee and an outsider, sees marriage to Katrina as a means of procuring Van Tassel's extravagant wealth ...