The story of Rip van Winkle takes a turn for the supernatural when the title character encounters strange men, dressed in antiquated traditional Dutch attire, playing nine-pins in a secluded area in the mountains. The men, who remind Rip of "the figures in an old Flemish painting," are mysterious and completely out of place, and maintain a grim silence even as they amuse themselves by bowling:
...[T]hey maintained the gravest faces, the most mysterious silence; and they were, withal, the most melancholy party of pleasure he had ever witnessed. Nothing interrupted the stillness of the scene but the noise of the balls, which, whenever they were rolled, echoed along the mountains like rolling peals of thunder.
It is after witnessing this surreal scene that Rip takes a drink of the men's liquor, whichobviously has some sort of magical properties, as it puts Rip to sleep for twenty years. This magical event serves as the turning point of the entire story, as Rip awakes to find that everything in his world has changed.
The major supernatural event in "Rip Van Winkle" is Rip's falling asleep for twenty years. We are prepared for this when Rip, on one of his rambles, meets mysterious people in a secluded section of the Catskills, wearing old-fashioned Dutch clothing. Rip has entered a supernatural realm in which the normal operations of time have been altered and time has apparently been drastically slowed down. In another instance of the supernatural, when Rip awakes, his Dutch companions and everything associated with them has disappeared, suggesting that he has re-entered "normal" time.
We should note that the tale is, in part, based on European folklore, and that the dreamlike supernatural segment is perhaps the most vividly described part of the story. The tale is, in fact, a hybrid of an Old World fairy tale and a realistic story about the birth of a new nation based on republican principles that "wake it up" from a stupor.