In the Catskill Mountains, farmer Rip Van Winkle meets a strange dwarf and a group of men playing ninepins. He drinks from their keg and falls into a deep sleep. When he awakens, everything is changed.

Connecticut Yankee Ichabod Crane arrives in the rural Dutch community of Sleepy Hollow and assumes his post as the new schoolteacher. Though the outsider is widely regarded with suspicion, the daughter of the area's wealthiest farmer, Katrina Van Tassel, is charmed by his manners and education. Ichabod's attentions to Katrina are not welcomed by blacksmith Brom Bones and when Brom tries to scare Ichabod by posing as the "Headless Horseman" of local...