Diedrich Knickerbocker, an older New York gentleman fascinated in the history and tales told by the descendants of Dutch settlers in New York in the early nineteenth century, narrates the story of Rip Van Winkle, a plain, kind-hearted man who lives in a little village in the Catskills.

Despite hailing from a history of chivalrous and militarily successful men, Rip is unconcerned about such matters and is more concerned with avoiding his nagging wife, Dame Van Winkle, and evading his responsibilities to his home and family. He spends the remainder of the day outside with his dog Wolf, away from his wife’s grasp, socializing with inn guests, hunting squirrels, fishing, or working on farms other than his own.

Rip eventually seeks safety in the woods with his gun and dog after Dame Van Winkle’s unrelenting pursuit of him. He follows a squirrel deep into the Catskill Mountains and eventually falls asleep. Rip is about to travel back down the mountain as the day’s light fades when he encounters a stranger.

Rip, motivated by an unexplained power, helps the stranger carry a large keg to the crest of the mountain, where he encounters strange guys dressed in historical garb playing ninepins.The drink Rip is meant to offer them is so appealing that Rip discreetly tries it before indulging in an excessive amount and passing out on the mountain.

Rip believes he slept all night when he wakes up and is worried about Dame Van Winkle’s response when she finds out. But it doesn’t take long to notice that something unusual has occurred. His beard has grown to be a foot long, and the gun beside him is an old, rusted model. He has stiff joints and struggles to ascend the mountain. He attempts to locate the top where he dozed asleep but is unsuccessful.

After spending as much time as he could seeking for Wolf, who is also missing, Rip hesitantly descends the mountain with the ancient rifle, fearing a meeting with his wife.Rip successfully returns to the settlement despite the fact that the route is nowhere to be found and the surroundings are bizarre.

A bunch of strange youths pursue Rip on the outside of the settlement, pointing at his beard. Rip notices that the community has increased in size and people. New homes line the streets, as strangers peer out the windows at him. Rip finds his old residence and is perplexed. He expects to hear his wife shout at him, but never does. Furthermore, his residence appears to have been neglected for quite some time, as it is in disrepair.

He sees a dog who looks like Wolf, but Wolf is filthy and hungry, and the dog doesn’t know Rip. He goes to the inn in quest of his old friends, but instead finds the Union Hotel.When Rip introduced himself to the hotel guests as a “faithful subject of the monarch,” they were astonished.

He discovers that it has been 20 years since he last climbed the peak. There has been a revolution in America. Nicholas Vedder and Brom Ducher, two of his friends and neighbours, have died, while Derrick Van Bummel works for the newly created American Congress. His daughter Judith has married and had a child, and his son Rip Van Winkle Jr. has grown up to be just like his father (Rip Van Winkle III).

The oldest man in town, Peter Vanderdonk, validates and explains Rip’s narrative on the mountain, and the residents eventually come to trust him, shifting their attention back to the upcoming presidential election. Rip goes in with his daughter and continues to live his life as he did before going away, except that he is now free to enjoy it without fear of his wife’s intervention.