The larger changes in society are yet more profound. Rip went to sleep a subject of George III and has awakened a citizen of the United States of America under the leadership of George Washington. Although Rip soon falls into his old loitering ways, justified now by his white beard and the absence of matrimonial demands, it takes him some time to absorb the Revolution that has run its full course while he slept. The town has learned to accommodate the new republic, and all the changes lend charm to Rip’s fresh recollections of the old order. Rip tells and retells his story, which is accepted most readily by the older Dutch villagers, who have kept alive a legend that Hendrick Hudson’s men keep a vigil in the nearby mountains and play at ninepins there regularly in the afternoon. Rip prefers the company of the young, however, not so much to be in touch with the new as to preserve the old in a relentlessly changing world.
Rip’s night in the woods symbolizes the fantasy of escape through one’s imagination, which is in itself a form of storytelling. Once he is freed of his duties to his family, he becomes the town storyteller, and it is this story which has freed him from his domestic duties—he literally and figuratively dreamed them away. In this way the imagination, or one’s creative life, is presented as a way to deal with the less pleasing duties of everyday life. At the same time, it is not without its dangers. Although Van Winkle finds a happy ending, he is very close to being labeled insane or dangerous and being thrust out of the town.