The story takes place in the Catskill Mountains in New York, west of the Hudson river. The author describes the mountains as follows:

They are a dismembered branch of the great Appalachian family, and are seen away to the west of the river, swelling up to a noble height, and lording it over the surrounding county.

While the author doesn't give the story an exact date; at the end of the story he mentions General Washington. So the reader can presume, even given the time Van Winkle spends away from the village, that the story takes place around the early- to mid- eighteenth century.

Rip Van Winkle, the main character, lives on a farm with his family in a Dutch "village of great antiquity" at the foot of the mountains. He is so unfit for physical labour that the author states his farm was "the most pestilant little piece of ground in the whole country."

Midway through the story, Rip Van Winkle meets (who the author calls) the Old Man of the Glen on a grassy knoll at one of the highest points of the mountain. The old man takes Van Winkle to a small amphitheater where Van Winkle drinks beer and observes many "odd looking personage" playing nine ball and having fun.

Some years later, he wakes up back at the grassy knoll—a much older man—and heads back to what is a much changed village.

"Rip Van Winkle" is a story that spans both sides of the American Revolution and is focused on the transition away from a colonial identity to one forged by independence. It takes place in a small village in the Catskills and follows its title character—who retreats up into the mountains and ends up sleeping through twenty years. Thus, he misses the entire Revolution and awakens to a world very alien to the one he knew.

Rip was born to a particular time and culture that was grounded within the experience of colonial identity. As the story begins, we are introduced to Rip and to the quaint village in which he lives. After he awakens from his sleep, he returns to find this familiar world erased by the experience of the Revolution.

The setting of the story is the Catskill (or as the narrator spells them, Kaatskill) mountains of New York. The narrator calls them "fairy" mountains, and so they will prove to be.

The story primarily takes place at the foot of the Catskills, in a "Village" of "great antiquity," founded by the Dutch. Some of the villagers, including Rip van Winkle, live in the original yellow brick houses with latticed windows built by the first Dutch settlers.

Another setting is the mysterious mountain pass into which Rip one day wanders, where he meets people dressed in old fashioned Dutch clothing who bowl and give him beer that puts him to sleep for twenty years.

The picturesque, sleepy "Village" that was so quiet and "antique" for many years has changed when Rip returns to it after his long rest. No longer does the portrait of King George III hang over the inn: it has been replaced with one, "blue and buff," of George Washington. No longer are people as apathetic as they were in Rip's day: everyone now is bustling with energy as they participate in the politics of the new republic of the United States.

The story of "Rip Van Winkle" is told by a fictional man named Diedrich Knickerbocker. It takes place in the 1700s. New York was once a Dutch colony called New Holland. Even after New Holland became New York in the late 1600s, Dutch influence and culture remained.

Just to the west of the Hudson River in New York lie the Catskill Mountains. These mountains are "a dismembered branch of the great Appalachian family." The main character, Rip Van Winkle, lives in a small village "at the foot of these fairy mountains." This village is the setting of the beginning and of the end of the story. In the middle part of the story, Rip Van Winkle ventures out into the Catskill Mountains. It is there that he encounters a strangely dressed group of people playing a game of nine-pins. He drinks with them and then falls asleep. He sleeps in the mountains for twenty years before returning to his village.

Where is the story of "Rip van Winkle" set?

In a literal sense the story takes place in old New York, in (as Irving announces in the very first sentence) the Catskill Mountains overlooking the Hudson River. As is typical of early Romantic literature, the setting is a picturesque one. Writers from this period loved to describe the beauty of nature, as a counterpoint to the artificiality of the urban milieu that was becoming increasingly dominant in both Europe and America at that time. But this specific literary tendency was also a reaction against the eighteenth-century Enlightenment and its emphasis upon man and man's works, his progress, his advancement and his overcoming of Nature in creating a modern world based on science and achievement. Irving, like the German Romantic writers who preceded and influenced him, seems to revel in the natural world for the beauty of the words he's able to use in describing it:

They [the Catskills] are a branch of the great Appalachian family, and are seen away to the west of the river, swelling up to a noble height, and lording it over the surrounding country. Every change of season, every change of weather, indeed, every hour of the day, produces some change in the magical hues and shapes of these mountains.

The Catskills are called "fairy mountains," befitting the fairy-tale atmosphere of the story, typically so for the early nineteenth century, in which writers reinterpreted the past and the magical, mysterious features of the pre-modern world they sought to recreate. Yet all of this is a metaphor for the action that takes place within Rip van Winkle's mind. In his sojourn on the mountain we have no way of knowing how much of what he experiences is real and how much is imaginary. The strange traveler dressed in "antique Dutch fashion," the men playing ninepins looking like "the figures in an old Flemish painting," are projections of Rip's soul, of the dreamer within him who wishes to escape the tedious real world in which he's henpecked by his wife, and where he doesn't fit in with the times as they march forward inexorably.

That march forward is what passes Rip by during his long sleep. The setting remains the same after he awakens—the same in a topographic or geographic sense, that is, since he's still in the Catskill region of New York. But now New York is part of a new country, the United States. So in a way what he experiences is a transference from the old milieu—and the even older one in which his dreamer's mind has plunged him—into a modern, transformed world. The story is a kind of parable about man's inability to remain apart from the dynamic process of human life, though Nature is implicitly the one constant that stands apart from the ceaseless changes created by man, and which Rip is alienated by. Thus the setting in the beautiful mountains and the Hudson Valley are one with Rip, even while human activity exists in a different realm.

Where is the story of "Rip van Winkle" set?

"Rip Van Winkle" takes place during the mid-18th century in an unnamed village in the Catskill Mountains of upstate New York. The setting is very important to the story as the Catskills are a place where strange and mysterious things tend to happen. As Washington Irving himself once said, the Catskills bewitched his boyish imagination. In writing "Rip Van Winkle," Irving was mining a rich seam of local legend. According to Native American folklore, the Catskills were the dwelling place of spirits. And the Dutch settlers who lived there—like old Van Winkle himself—often claimed to experience all manner of marvelous events and appearances. In such a magical environment it doesn't seem all strange that a man should fall asleep under a tree for twenty years.