"The Legend of Sleepy Hollow" is a short story of speculative fiction by American author Washington Irving, contained in his collection of 34 essays and short stories entitled The Sketch Book of Geoffrey Crayon, Gent.. Written while Irving was living abroad in Birmingham, England, "The Legend of Sleepy Hollow" was first published in 1820. Along with Irving's companion piece "Rip Van Winkle", "The Legend of Sleepy Hollow" is among the earliest examples of American fiction with enduring popularity, especially during Halloween because of a character known as the Headless Horseman believed to be a Hessian soldier who lost his head to a cannonball in battle.

The story is set in 1790 in the countryside around the Dutch settlement of Tarry Town (historical Tarrytown, New York), in a secluded glen called Sleepy Hollow. Sleepy Hollow is renowned for its ghosts and the haunting atmosphere that pervades the imaginations of its inhabitants and visitors. Some residents say this town was bewitched during the early days of the Dutch settlement. Other residents say an old Native American chief, the wizard of his tribe, held his powwows here before the country was discovered by Master Hendrick Hudson.

The most infamous spectre in the Hollow is the Headless Horseman, said to be the ghost of a Hessian trooper that 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".The "Legend" 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 a 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.