The story is set in 1790 in the countryside around the Dutch settlement of Tarry Town (historical Tarrytown, New York), in a secluded glen known as 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, while others claim that the mysterious atmosphere was caused by an old Native American chief, the "wizard of his tribe ... before the country was discovered by Master Hendrik Hudson." The most infamous spectre in the Hollow is the Headless Horseman, supposedly the ghost of a Hessian trooper whose head had been shot off by a stray cannonball during "some nameless battle" of the Revolution, 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 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. Bones, the local hero, unable to force Ichabod into a physical showdown to settle things, plays a series of pranks on the superstitious schoolmaster. The tension among the three continues for some time, and is soon brought to a head. On a placid autumn night, the ambitious Crane attends a harvest party at the Van Tassels' homestead. He dances, partakes in the feast, and listens to ghostly legends told by Brom and the locals, but his true aim is to propose to Katrina after the guests leave. His intentions, however, are ill-fated.

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