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.

Adaptations of two famous stories by Irving: The first of Ichabod Crane and his encounter with the headless horseman, and the second about Rip Van Winkle, who fell asleep and awakened twenty years later.

In the first of these stories from the Catskill Mountains, a superstitious schoolmaster encounters a headless horseman; in the second, a man sleeps for twenty years, waking to a much-changed world.