Rip Van Winkle
By Washington Irving (1783-1859)
A Study Guide
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Type of Work and Source
Publication Information
The Game of Ninepins
The Catskills as a Character
Author Information
Study Questions
Essay Topics
Free W. Irving Texts
Plot Summary
By Michael J. Cummings...© 2006
.......At the foot of the Catskill Mountains of New York was a picturesque village founded by Dutch colonists. Approaching it, one would see gabled homes with smoke curling up from the chimneys and shingle roofs reflecting the sunlight. 
.......A simple, easygoing man named Rip Van Winkle lived in this village, in a weather-beaten house, at the time when New York was an English colony. He was a descendant of the Van Winkles who served with distinction under Peter Stuyvesant in his struggles against Swedish settlers at Fort Christina (in present-day Delaware). 
.......Because he was kind and gentle, Rip was popular with all of his neighbors. Children especially loved him, for he would play with them, make them toys, and tell them stories. No one had a cross word for Rip–except his wife, who, taking advantage of his meekness, regularly nagged him. Her treatment of him earned Rip the sympathy of other wives. 
.......His only weak point was his inability to work for profit. It was not that he lacked patience or perseverance; for, as the narrator points out, “He would sit on a wet rock, with a rod as long and heavy as a Tartar’s lance, and fish all day without a murmur, even though he should not be encouraged by a single nibble.” Moreover, he was always ready to help a neighbor with hard work and frequently ran errands and did odd jobs for housewives. But when it came time to tend his own farm and keep up his own property, he was of little use. Fences would collapse, a cow would run off, and rain would fall at the very moment he decided to work. The only plants that thrived on his farm were weeds. Consequently, he had the least productive and least attractive farm in the area.
.......One of his children, little Rip, seemed to take after his father. Not only did he look like the elder Rip but he also wore Rip’s hand-me-down clothes, including a pair of galligaskins (loose-fitting trousers) which he would continually hitch up with one hand. 
.......Dame Van Winkle ceaselessly browbeat Rip for his failings, saying he was bringing the family to ruin. Rip would shrug and go outside, out of range of her scolding tongue. She treated his dog, Wolf, the same way, and Wolf began to resemble Rip in submissiveness. Rip often sought refuge with a village group that convened on a bench in front of an inn to gossip, tell stories, and on one occasion discuss events reported in a newspaper left behind by a traveler. The village schoolmaster, Derrick Van Brummel, would read the newspaper accounts. Old Nicholas Vedder, the owner of the inn, was the gray eminence of this group, guiding its thought and conversation even though he did little more than smoke his pipe and shift his position on the bench to remain in the shade of a tree. Unfortunately for Rip, Dame Van Winkle would sometimes come to the inn for him and haul him off, all the while her tongue lashing him and his compatriots, including Vedder. 
.......To escape his wife and the drudgery of his farm, Rip would sometimes head into the woods with Wolf and his gun. One day, high in the Catskill Mountains, he hunted squirrels, firing one shot after another. Hours later, tired from all the activity, he decided to lie down for a rest on a green knoll overlooking the rich forests and the Hudson River in the distance. When evening neared, he got up to return home, heaving a sigh at the thought of Dame Van Winkle and the terror of her tongue. At that moment, a man came up the mountain, calling out Rip’s name. Rip and Wolf both came to attention. As the man neared, Rip noticed that he was short and squat, with a beard and bushy hair, and wore old-fashioned Dutch clothes with buttons down the sides of his breeches. He was carrying a keg–probably liquor, Rip thought–and beckoned for Rip to help him. Always ready to assist others, Rip did so. As they ascended the mountain, Rip heard rumbling, like thunder, coming from a ravine. After they passed through it, they came to a hollow bordered by cliffs with overhanging trees; it resembled an amphitheater. There, Rip saw bearded men–all dressed like his companion and all of odd appearance, one with a large head and one with a large nose–playing ninepins. They neither spoke nor smiled. When they rolled their balls toward the pins, Rip again heard peals of thunder.
.......Upon the arrival of Rip, the players stopped and stared at him, unnerving him. His companion opened the keg and emptied it into flagons, then motioned for Rip to serve the players, which he did. After the strange men resumed their game, Rip began to feel at ease and decided to sample the brew. It was excellent. He drank another, then another and another. By and by, the liquor had a heavy effect, and he drifted into a deep sleep. 
.......When he woke up to a sunny morning, he was on the same green knoll upon which he rested when he first saw the man with the keg. His mind reviewed the events of the night before–the men, the ninepins, the liquor. Dame Van Winkle would give him a severe scolding this time. He reached out for his gun but was surprised to find that its barrel was rusted and its stock eaten away by worms. Perhaps those bowlers had stolen his gun and replaced it with a sorry old firelock. Wolf was nowhere to be found. When he arose to return to the place of the previous night’s revels to look for Wolf and retrieve his gun, he discovered that he was stiff in the joints. 
“These mountain beds do not agree with me,” thought Rip, “and if this frolic should lay me up with a fit of the rheumatism, I shall have a blessed time with Dame Van Winkle.”
.......However, the path he had walked with the strange man was now a mountain stream. Moreover, at the place where he entered the ravine, there was now only a wall of rock. Dumfounded, he returned to the village but was further puzzled when he saw people he did not recognize, all wearing strange fashions. Stroking his chin in bewilderment, he discovered that he had a beard a foot long. 
.......The village was larger than when he left it, with more people. He saw strange houses with strange names over the doors. Dogs barked at him and children made fun of him. When he reached his house, he saw an old, deteriorating dwelling with broken windows and a collapsed roof. An old dog outside–was it Wolf?–growled at him. Inside, he looked about but found only emptiness. Immediately, he walked over to the inn–but it was gone. In its place was a ramshackle building with these words painted on the door: “The Union Hotel, by Jonathan Doolittle.” There were men outside–but none that he recognized. One man was speaking loudly about “rights of citizens–election–members of Congress–liberty–Bunker’s Hill–heroes of ’76–and other words, that were a perfect Babylonish jargon to the bewildered Van Winkle.”
.......The men gathered around him and eyed him, for he was a strange sight to them. Women and children from the village also came to look at the peculiar man with the long beard and odd clothes. One man asked him how he voted. (Apparently, it was election day.)  Another asked whether he was a Federal or a Democrat. A third man with a cane, seeing the old gun, asked whether Rip had come to the village to start a riot. Rip told them, ““I am a poor quiet man, a native of the place, and a loyal subject of the king, God bless him!” At that, they declared him a Tory and a spy. 
.......The man with the cane calmed the others down and inquired again why Rip had come to the village. Rip assured him he meant no harm, then inquired where his neighbors were, naming them one by one: Nicholas Vedder, Brom Dutcher, Van Brummel the schoolmaster. Vedder has been dead 18 years, Rip was told. Dutcher went off to war and never returned. Van Brummel, too, went off to war, attained the rank of general, and got himself elected to Congress. All these replies puzzled Rip. 
.......Then he said, “Does nobody here know Rip Van Winkle?” One man replied,  “Oh, to be sure! that's Rip Van Winkle yonder, leaning against the tree.”
.......The fellow looked exactly like Rip and even wore ragged clothes. When a man asked Rip his name, he said he did not know, for he now doubted his own identity. A woman named Judith Gardenier came up just then holding a child named Rip. When Rip asked her who her father was, she replied,  “Ah, poor man, his name was Rip Van Winkle; it’s twenty years since he went away from home with his gun, and never has been heard of since—his dog came home without him; but whether he shot himself, or was carried away by the Indians, nobody can tell. I was then but a little girl.” She also mentioned that her mother had died when she suffered a broken blood vessel shouting at a peddler. Rip then identified himself.
.......“I am your father!” cried he–“Young Rip Van Winkle once–old Rip Van Winkle now!–Does nobody know poor Rip Van Winkle!” 
.......An old woman stepped forward for a closer look at him and confirmed that he was indeed Rip Van Winkle. When she asked where he had been for twenty years, Rip told his story to everyone. The people, skeptical, winked at one another or shook their heads. It happened that the oldest inhabitant of the village, Peter Vanderdonk, was coming up the road, and he was asked for his opinion. He immediately identified Rip. In addition, it was a fact, the narrator reports him as saying, that strange beings had always roamed the Catskills and that Henrdrick Hudson, the discoverer of the region, visited the area every twenty years with the crew of his ship, the Half-Moon, to “keep a guardian eye upon the river.” The narrator further reports that Vanderdonk’s father once observed Hudson and the crew playing ninepins in the mountains and that Vanderdonk himself once heard the thunderous sound of their rolling balls.
.......The crowd then disbanded. Rip went to live with his daughter and her farmer husband. Rip’s son–the man leaning against the tree–had been hired to work the farm but spent all his time on his own interests. Rip went for walks, took up his old habits, and even found a few of his old friends. However, he preferred the company of the younger generation. 
.......At an age when he could do as he pleased, which was to say nothing, he began sitting on the bench in front of the Doolittle's Hotel. There the villagers looked upon him as one of their patriarchs. In time, he learned that their had been a revolutionary war in which the country broke from England and that he was now a citizen of the United States. Overall, he was a happy man and was especially pleased to be free of the tyranny of Dame Van Winkle. 
.......From time to time, he told his story to strangers and eventually everyone in the village knew all the details by heart. Some inhabitants still doubted the tale, but old-timers swore by it and even claimed, whenever they heard a thunderstorm, that Hendrick Hudson and his crew were playing ninepins again. 


The story begins about five or six years before the American Revolution and ends twenty years later. The action takes place in a village in eastern New York, near the Hudson River and the Catskill Mountains. The river was named after Englishman Henry Hudson, who explored it in 1609. The Catskill Mountains were named after Kaaterskill, the Dutch word for a local stream, Wildcat Creek. The Catskills contain many other streams, as well as lakes, waterfalls, and gorges. 


Rip Van Winkle: Meek, easygoing, ne’er-do-well resident of the village who wanders off to the mountains and meets strange men playing ninepins.
Dame Van Winkle: Rip’s nagging wife.
Nicholas Vedder: Owner of a village inn where menfolk congregate.
Derrick Van Brummel: Village schoolmaster.
Wolf: Rip’s dog.
Man Carrying Keg Up the Mountain: Spirit of Englishman Henry Hudson, explorer of the Hudson River.
Ninepin Bowlers: Henry Hudson’s crewmen from his ship, the Half-Moon.
Brom Dutcher: Neighbor of Rip who went off to war while Rip was sleeping.
Old Woman: Woman who identifies Rip when he returns to the village after his sleep.
Peter Vanderdonk: Oldest resident of the village. He confirms Rip’s identity and cites evidence indicating Rip’s strange tale is true. 
Judith Gardenier: Rip’s married daughter. She takes her father in after he returns from his sleep. 
Mr. Gardenier: Judith’s husband, a farmer.
Rip Van Winkle II: Rip’s ne’er-do-well son.
Rip Van Winkle III: Rip’s infant grandchild. Its mother is Judith Gardenier.
Van Schaick: Village parson.
Jonathan Doolittle: Owner of the Union Hotel, the establishment that replaced the village inn. 
The Catskill Mountains: See Personification.
Various Men, Women, and Children of the Village

Type of Work, Source, and Publication Information

"Rip Van Winkle" is a short storyone of America's most belovedbased on German folk tales. It was first published in a collection of Irving's works called The Sketch Book (1819-1820). 


Change With Continuity and Preservation of Tradition

After Rip awakens from his long sleep and returns to the village, he does not recognize the people he encounters. But not only their faces are new but also their fashions and the look of the village: It is larger, with rows of houses he had never seen. His own house is in shambles now with no one living in it, and the inn he frequented is a hotel. His wife and old Vedder are dead. Others left the village and never came back. Everything is different, it seems; nothing is as it was. There has even been a revolutionary war in which America gained its independence from England and became a new country. However, when Rip looks beyond the village, he sees that the Hudson River and the Catskill Mountains are exactly the same as they were before his sleep. He also begins to encounter people who knew him long ago: first, the old woman, then the old man, Peter Vanderdonk, who testifies to the truth of Rip’s strange tale about the ninepin bowlers he met in the mountains. At this point in the story, Irving’s main theme begins to emerge: Although wrenching, radical changes are sometimes necessary to move society forward, such changes must not eradicate old ways and traditions entirely. Real, lasting change is an amalgam of the old and new. New builds on the foundations of the old. There must be continuity. So it is that old Vanderdonk, in confirming Rip’s tale, says he himself has heard the thunder of ninepin bowlers, who are the crewmen of The Half-Moon, the ship Henry Hudson captained in his exploration of the Hudson River. It seems that their spirits return to the Hudson Valley and Catskill Mountains every twenty years to keep a “guardian eye” on the river and its environs. Hudson was an Englishman, yes, but his association with his overthrown country does not mean the values he represents must die with the revolution. Rip also sees his son, Rip II, now a grown man, who looks just like him, and is reunited with his daughter, now a grown woman, who is holding an infant–Rip III. Thus, though, change has come to the village, their remain links with the past; there is continuity. New generations come along that bring change, but old values and traditions–as well as family lines–remain alive and thriving. And, every now and then, thunder rumbles in the Catskills when Hudson and his crew play ninepins.

The Magic of the Imagination

Irving’s story suggests that human imagination can can give society charming, humorous stories that become part of an enduring, magical folklore. Today, the Catskill and Hudson Valley regions well remember Rip Van Winkle and Ichabod Crane–the hero of another Irving story, “The Legend of Sleepy Hollow”–as if they were real persons. A bridge across the Hudson has even been named after Rip. Sunnyside, Irving’s Tarrytown home between 1835 and 1859, is a major tourist attraction in the Hudson Valley. 


The climax of the story occurs when the townspeople recognize Rip after he returns to his village. 

The Game of Ninepins

Ninepins is a game (or sport) in which a participant rolls wooden balls on a lane in an attempt to knock down nine bottle-shaped wooden pins arranged in the shape of a diamond. The participant may bowl up to three balls to knock down all the pins. Ninepins is similar to the modern sport of bowling.

Personfication: The Catskills as a Character

At the outset of his story, Washington Irving uses personification to invest the Catskill Mountains with human qualities. Irving tells us in Paragraph 1 that they are part of a “family,” the Appalachian family. And they are a proud, majestic member of that family, “lording it over the surrounding country.” They are also active rather than passive, reacting to the weather and the seasons with changes in their “magical hues and shapes.” In fair weather, “they are clothed in blue and purple.” But sometimes, even though the sky is cloudless, they will gather a hood of gray vapors about their summits, which, in the last rays of the setting sun, will glow and light up like a crown of glory.
Making the mountains come alive enables them to become mysterious and unpredictable; they may even play tricks on those who venture within their confines. 


"Rip Van Winkle" was written by Washington Irving (1783-1859), a lawyer who pursued a writing career after he discovered that practicing law did not interest him. At a time when most Americans read British authors almost exclusively, Irving proved that American writers could compete with their British counterparts. He was among the first American writers who gained an international reputation by writing short stories. Irving had a special talent for creating a magical, fairytale quality in his talesnotably "Rip Van Winkle" and "The Legend of Sleepy Hollow"and thus helped shape the folklore of early America. His elegant writing style, full of gentle humor and vivid descriptions, continues to enchant modern readers. It is likely that his engaging stories will remain popular for ages to come. 


Study Questions and Essay Topics

  • Even though he was a failure as a farmer, Rip Van Winkle was a success as a human being. What were the most praiseworthy qualities that he possessed?
  • In what way does Irving's portrayal of Dame Van Winkle help to illumine Rip's character?
  • Write a short essay (or a paragraph or two) that uses personification and/or other figures of speech to invest with a personality the natural surroundings where you live, as Irving did in "Rip Van Winkle." (See "Personification: The Catskills as a Character.")
  • If you fell asleep today and awakened 20 years from now, what questions would you ask the first person you saw? 
  • When Rip returns to his village, he learns that Dame Van Winkle has died and that his fellow Americans liberated themselves from English rule in a revolutionary war. What do the war and the death of Rip's wife have in common in terms of how Rip will live the rest of his life?
  • Although "Rip Van Winkle" is a fictional tale, it presents truths that can teach the reader. Write an essay that focuses on the truths presented in the short story.