Watch The Night of the Headless Horseman (1999) : Full Movie Online Free The teacher Ichabod Crane arrives at Sleepy Hollow town and immediately falls in love with Katrina Van Tassel. Ichabold is intelligent, but weak and coward, and he finds a competitor, the strong Brom Bones that has been wooing Katrina for a long time. Soon begins a competition between the two men for Katrina, but Ichabold's greatest problem is the Headless Horseman that haunts him.