 In a small town named Sleepy Hollow, a gangly schoolteacher named Icabod Crane comes to town. Despite his unattractive appearance, he quickly proves to be a ladies man who charms the local beauty, much to the local tough, Brom Bones , displeasure. A subtle rivalry erupts, only to have Crane continually gaining the upper hand. The situation changes when Brom learns of Crane s superstitions and exploits them as he musically tells the legend of the fearsome Headless Horseman to frighten the teacher. That night, Crane s lonely night ride home becomes more lively than he ever imagined as the Horseman appears to chase him.