The adventures of Rip van Winkle come about because he eschews work of any kind and he wishes to escape the harping of his wife, who is described as a "termagent." Dame van Winkle represents the Puritan, the voice of duty and responsibility, so when Rip ascends the mountain with an odd little Dutchman who bears a large keg on his shoulder, he flees duty and, instead, occupies himself with watching the strange little grave-faced men engage in odd activities. When pressed upon to pass around large flagons into which the liquid of a large keg has been emptied, Rip takes a few swallows himself. Afterwards, he falls into a deep sleep from having consumed this strange libation.

When Rip awakens twenty years later--unknown to him, of course--his first thoughts are of Dame van Winkle: "Surely...I have not slept here all night." As he recalls the odd little man with a keg of liquor and the other strange occurrences of his memory, Rip regrets "ah! that flagon! that wicked flagon!....what excuse shall I make to Dame van Winkle?" Then, he tries to find his gun and dog, but sees a only rusted gun instead. So, he descends the mountains, noticing a new stiffness in his joints. Upon reaching his house with some difficulty, Rip expects to "hear the shrill voice of Dame van Winkle," but he sees only that the house "has gone to decay" and his wife is not there. The disarray that Rip sees, along with the empty echoes of his voice, disturb him.

Rip, then, hastens to the inn where he finds things much changed. Instead of George III, there is the portrait of another George, George Washington; moreover, his old cronies reject him, while he stands by the inn. But, he learns that he is a "free citizen of the United States, and he can come and go without fear of the "tyranny of Dame Van Winkle":

Whenever her name was mentioned, however, he shook his head, shrugged his shoulders, and cast up his eyes, which might pass either for an expression of resignation to his fate or joy at his deliverance.