High School English · American Short Stories · Unit 2
Washington Irving: Legends of the Hudson
A man who sleeps through a revolution, a schoolmaster who rides off into a legend, and a storyteller who will not quite promise that any of it is true.
Two hundred years ago, American readers were often told that their young country had no stories of its own. Its books came from London. Then a New Yorker living in England sent home a series of small paperbound booklets, and two of the tales in them took hold for good. One is about a man who naps in the mountains for twenty years. The other is about a schoolmaster, a pumpkin and a ghost with no head.
This unit looks at how Washington Irving made them work. He took old European folk tales, moved them to the Hudson River valley, and told them through a narrator who keeps winking at you. You will learn to spot that wink: the frame narrator, the tall tale told with a straight face, and endings that leave a little room for doubt.
On this page: his life and pen names, a storyteller’s toolkit, a guide to each story (summary, craft notes and questions), where the stories came from, why Irving matters, a note on period attitudes, a reading game, a quiz, and questions that connect the two stories.
Before you read. Both stories appeared in 1819 and 1820 and are set in the years around the American Revolution. They are comedies, but they carry the attitudes of their time. Black characters in “The Legend of Sleepy Hollow” appear only in the background and are described as racist caricatures, and slavery was still legal in New York when the story takes place. Native Americans appear only as figures in old legends, and the humor about wives and women is often unkind. We do not reprint those passages; our note on period attitudes explains.
His Life: From Manhattan to England and Back to the Hudson
Washington Irving was born in Manhattan on April 3, 1783, the year the Revolutionary War ended. He was one of eleven children in a merchant family, and he was named after George Washington. Late in life he wrote Washington’s biography.
- 1783–1798 · New York. Irving is a restless student who likes adventure stories and the theater. In 1798 an outbreak of yellow fever in Manhattan sends him upriver to Tarrytown, where he stays with his friend James Kirke Paulding. There he comes to know the valley’s Dutch customs and its ghost stories.
- 1802–1809 · First writing. In 1802 he writes humorous letters to the Morning Chronicle as “Jonathan Oldstyle.” He tours Europe from 1804 to 1806, then barely passes the bar exam in 1806. In 1807 he starts the comic magazine Salmagundi with his brother William and Paulding. On December 6, 1809, he publishes A History of New York, a satire, under the name Diedrich Knickerbocker.
- 1815–1818 · England. In mid-1815 he sails to England to help save the family trading business. He meets the Scottish novelist Walter Scott in 1817. The business goes bankrupt in 1818, and Irving decides to try living by writing. That year, staying with his sister Sarah and her husband, Henry van Wart, in Birmingham, England, he writes “Rip Van Winkle” in one night.
- 1819–1820 · The Sketch Book. The Sketch Book of Geoffrey Crayon, Gent. comes out in New York in seven paperbound installments, printed by C. S. Van Winkle. “Rip Van Winkle” is in the first, dated June 23, 1819. “The Legend of Sleepy Hollow” is in the sixth, on March 15, 1820. With Scott’s help, the London publisher John Murray takes on the British edition. It is a hit on both sides of the Atlantic.
- 1820–1832 · Europe. He stays abroad, writing and traveling, including years in Spain. He arrives home in New York on May 21, 1832, after 17 years away.
- 1835–1859 · Sunnyside. In 1835 he buys a cottage near Tarrytown, a short ride from the real Sleepy Hollow, and later names it Sunnyside. He serves as the U.S. minister to Spain from 1842 to 1846, and he finishes a five-volume Life of George Washington in 1855–59. He dies at Sunnyside on November 28, 1859, at 76, and is buried in Sleepy Hollow Cemetery.
One fact surprises most readers. Irving set “Rip Van Winkle” in the Catskill Mountains, but he later admitted, “When I wrote the story, I had never been on the Catskills.” He had seen them from a boat on the Hudson. The mountains in the story come from that view, and from his imagination.
Crayon and Knickerbocker: Stories Told by Someone Else
Irving almost never spoke to readers in his own name. He invented narrators, gave them personalities, and let them tell the stories. Two matter for this unit.
- Diedrich Knickerbocker (1809). Before A History of New York came out, Irving played a prank on the city. He placed notices in the New York Evening Post asking for news of Diedrich Knickerbocker, a crusty old Dutch historian who had supposedly gone missing from his hotel. A later notice, said to be from the hotel’s owner, warned that if Knickerbocker did not come back and pay his bill, the owner would publish a manuscript he had left behind. Readers followed the story, and some city officials worried enough to offer a reward. Then the “manuscript” appeared: Irving’s book. The name stuck. “Knickerbocker” became a nickname for New Yorkers, and the basketball team the New York Knicks is short for the Knickerbockers.
- Geoffrey Crayon (1819). The Sketch Book is signed by Geoffrey Crayon, Gent., a quiet American gentleman traveling in England who sketches what he sees in words, the way an artist sketches with a crayon. Most of its pieces are about England. Only a few deal with America.
Here is the clever part. In The Sketch Book, Crayon says both American tales were “found among the papers of the late Diedrich Knickerbocker.” So the stories pass through several hands: Irving invents Crayon, who passes along papers from Knickerbocker, who heard the tales from the old Dutch people of the Hudson Valley. Every layer is a chance for a joke, and for doubt.
Ask yourself: why might a writer hide behind a made-up old historian instead of telling a ghost story in his own voice?
The Storyteller’s Toolkit
Five terms you will use in both stories.
Frame narrator
A frame story is an outer story that introduces the main one, like a picture frame around a painting. Here the frame is Crayon and Knickerbocker. A note after “Rip Van Winkle” and a postscript after “Sleepy Hollow” step back out of the tale and talk about where it came from.
The doubtful storyteller
Irving’s narrators keep saying they cannot be sure. In “Sleepy Hollow” the narrator says of a local legend, “I do not vouch for the fact,” and of a key scene, “in fact I do not know.” The pretended uncertainty is part of the fun, and it leaves room for you to decide what really happened.
Tall tale and mock seriousness
A tall tale is a story with unbelievable elements, told as if it were true. Irving adds mock seriousness: he treats small things with grand words. Knickerbocker insists Rip’s story “is beyond the possibility of doubt,” which is exactly why you should doubt it.
Legend and folklore
A legend is a traditional story about a place or person that people half believe. Both tales present themselves as local legends, passed from one teller to the next, and both end with what the neighbors still say “to this day.”
Setting and local color
Irving fills the stories with real places along the Hudson: the Catskills, the Tappan Zee, Tarry Town. He describes Dutch farm food, clothes and customs in loving detail. Later writers would call this kind of writing local color.
Watch for the wink. Irving rarely says a story is false. Instead he lets you notice things: a character who keeps changing his story, a rival who laughs too hard, a teller who admits he believes only half. As you read, mark every moment where the narrator seems to be smiling.
Rip Van Winkle
Story · first installment of The Sketch Book of Geoffrey Crayon, Gent., June 23, 1819 · Read it free at Project Gutenberg
Summary. The story opens with a view: “WHOEVER has made a voyage up the Hudson must remember the Kaatskill mountains.” In an old Dutch village at their foot lives “a simple, good-natured fellow, of the name of Rip Van Winkle.” Everyone likes him. He will help any neighbor and play with any child, but “The great error in Rip’s composition was an insuperable aversion to all kinds of profitable labor.” He “would rather starve on a penny than work for a pound.” His farm falls apart and his wife, Dame Van Winkle, scolds him without end. He escapes to the bench outside the village inn, under “a rubicund portrait of his Majesty George the Third,” or to the woods with his dog, Wolf.
One autumn day, high in the mountains, he hears a voice calling, “Rip Van Winkle! Rip Van Winkle!” A “short, square-built old fellow” in old Dutch clothes needs help carrying a keg. In a hollow, a company of odd, silent men in old-fashioned dress are playing ninepins, and the rolling balls echo “like distant thunder.” It is “the most melancholy party of pleasure he had ever witnessed.” Rip serves them from the keg, then sneaks a taste. It has the flavor of “excellent Hollands,” a Dutch gin, and he goes back to the flagon so often that “he fell into a deep sleep.”
He wakes to find “an old firelock lying by him, the barrel encrusted with rust” in place of his clean gun. Wolf is gone. “That flagon last night,” he thinks, “has addled my poor head sadly!” In the village he knows no one, and no one knows him, and he finds that “his beard had grown a foot long!” His house is a ruin. The inn is now “The Union Hotel, by Jonathan Doolittle,” with “a singular assemblage of stars and stripes” on a pole. On the old sign, King George’s red coat “was changed for one of blue and buff, a sword was held in the hand instead of a sceptre,” and the name below reads “GENERAL WASHINGTON.”
A busy crowd asks him “on which side he voted?” When he declares himself “a loyal subject of the King, God bless him!” they shout, “a tory! a tory! a spy! a refugee!” His old friends are dead or gone. In despair he cries, “I’m not myself--I’m somebody else.” Then a young woman with a baby says her father was Rip Van Winkle, but “it’s twenty years since he went away from home with his gun.” She is his daughter, Judith, and her mother has died. Old Peter Vanderdonk, the village historian, explains: Hendrick Hudson, the explorer, keeps “a kind of vigil there every twenty years, with his crew of the Half-moon.” For Rip, “the whole twenty years had been to him but as one night.” He moves in with his daughter, takes back his seat at the inn door, and becomes the village’s chronicle of the old times “before the war.”
Clues and craft
- Setting as history: the inn sign is the whole Revolution in one picture. The same face, repainted, goes from King George to General Washington. Rip slept through the birth of a nation.
- Humor: Rip’s big change in the new republic is personal. He no longer lives under “petticoat government,” the story’s joke about his wife. Notice what the story finds funny, and who pays for the joke.
- The doubt inside the story: when Rip first tells his tale, some neighbors “were seen to wink at each other, and put their tongues in their cheeks.” Later he is said to “vary on some points every time he told it.”
- The frame: Knickerbocker’s note insists, “I have even talked with Rip Van Winkle myself,” and concludes, “The story, therefore, is beyond the possibility of doubt.” The straight face is the joke.
Discussion questions
- Is Rip lazy, or is he kind? Can a character be both? Find one sentence that supports each view.
- The villagers ask Rip whether he is “Federal or Democrat.” What has changed about the village besides the faces?
- Some neighbors think Rip was “out of his head.” Write the most likely realistic explanation of the twenty years. Does the story let you believe it?
- Rip is happier after the Revolution, but not for political reasons. What is Irving saying about how ordinary people live through history?
The Legend of Sleepy Hollow
Story · sixth installment of The Sketch Book of Geoffrey Crayon, Gent., March 15, 1820 · Read it free at Project Gutenberg
The morning after: a hat by the brook, and “close beside it a spattered pumpkin.” Original art made for Jugami.
Summary. Near the village of Tarry Town, on the eastern shore of the Hudson where the river widens into the Tappan Zee, lies a little valley that is “one of the quietest places in the whole world.” “A drowsy, dreamy influence seems to hang over the land.” Locals say it was “bewitched by a High German doctor” in the early days. Its most famous spirit is “the apparition of a figure on horseback without a head,” said to be “the ghost of a Hessian trooper whose head had been carried away by a cannonball in some nameless battle during the Revolutionary War.” The Hessians were German soldiers hired by the British. This one rides “in nightly quest of his head.”
The schoolmaster, Ichabod Crane, is “a native of Connecticut.” “He was tall, but exceedingly lank,” and looks like “some scarecrow eloped from a cornfield.” He lives by turns in the farmers’ homes, “boarded and lodged at the houses of the farmers whose children he instructed.” He is “a perfect master of Cotton Mather’s History of New England Witchcraft, in which, by the way, he most firmly and potently believed,” and “No tale was too gross or monstrous for his capacious swallow.” He courts Katrina Van Tassel, “the daughter and only child of a substantial Dutch farmer,” while picturing her father’s land “readily turned into cash and the money invested in immense tracts of wild land.” His rival is “Abraham--or, according to the Dutch abbreviation, Brom--Van Brunt,” known as “BROM BONES,” a strong, prank-loving rider with “more mischief than ill-will in his composition.”
Ichabod rides a borrowed old plow horse named Gunpowder to an autumn party at the Van Tassel farm. After the dancing and a feast of “the doughty doughnut, the tenderer oily koek, and the crisp and crumbling cruller,” the guests swap war stories and ghost stories. In old Brouwer’s tale, the Horseman “suddenly turned into a skeleton, threw old Brouwer into the brook.” Brom tells of racing the Horseman to the church bridge, where “the Hessian bolted and vanished in a flash of fire.” Ichabod stays behind to speak with Katrina alone. “What passed at this interview I will not pretend to say, for in fact I do not know.” Whatever it was, he leaves looking crushed.
He rides home at “the very witching time of night,” past Major André’s tree, named for a British officer captured nearby in the Revolution. In the dark a huge rider falls in beside him and will not answer “Who are you?” Then Ichabod sees that the rider “was headless! but his horror was still more increased on observing that the head, which should have rested on his shoulders, was carried before him on the pommel of the saddle.” The chase races for the church bridge. “If I can but reach that bridge,” thinks Ichabod, “I am safe.” He crosses, looks back, and sees the rider “in the very act of hurling his head at him.” In the morning his horse is back at its master’s gate. By the brook “was found the hat of the unfortunate Ichabod, and close beside it a spattered pumpkin.” Ichabod is never seen in Sleepy Hollow again.
Then the story gives two endings. Years later an old farmer brings news that Ichabod is alive in another part of the country. He left out of fear and embarrassment, and he “had been admitted to the bar, turned politician, electioneered, written for the newspapers, and finally had been made a justice of the Ten Pound Court.” Brom marries Katrina, and he “was observed to look exceedingly knowing whenever the story of Ichabod was related, and always burst into a hearty laugh at the mention of the pumpkin.” But “The old country wives, however, who are the best judges of these matters, maintain to this day that Ichabod was spirited away by supernatural means.”
Clues and craft
- The ambiguous ending: Irving gives you a ghost and a prank, and he never chooses. The pumpkin and Brom’s laugh point to a joke. The country wives, and the plowboy who fancies he hears Ichabod’s voice “chanting a melancholy psalm tune,” keep the ghost alive.
- Planted clues: Brom loves pranks, rides like a demon, and tells a tale of racing the Horseman to that very bridge on the very night Ichabod meets him there.
- Character as cause: Ichabod believes every ghost story he hears. A man who reads Cotton Mather by firelight is the perfect victim for a headless rider.
- The postscript: Knickerbocker says he heard the tale from “a pleasant, shabby, gentlemanly old fellow in pepper-and-salt clothes.” Asked for the moral, the old man jokes that being turned down by an heiress is “a certain step to high preferment in the state,” then admits, “I don’t believe one-half of it myself.”
Discussion questions
- Was it Brom or a ghost? Build the strongest case for each side, then decide which the story supports more.
- Why do you think Irving refuses to tell us what Katrina said to Ichabod?
- Ichabod wants Katrina mostly for her father’s farm. Does the story want you to feel sorry for him?
- Ichabod ends up a lawyer, a politician and a judge. Is that a punishment, a reward, or a joke about American success?
Where the Stories Came From
Irving did not invent these plots from nothing. He borrowed from European folklore, then moved the borrowed stories to the Hudson Valley. Encyclopaedia Britannica calls the two tales “Americanized versions of German folktales.”
- A sleeping emperor. In his note after “Rip Van Winkle,” Knickerbocker admits the tale might seem to come from “a little German superstition about the Emperor Frederick der Rothbart and the Kypphauser mountain.” In German legend the medieval emperor Frederick Redbeard (Barbarossa) sleeps inside the Kyffhäuser mountain until he is needed.
- A German goatherd. Scholars widely think Irving also drew on “Peter Klaus,” a German folk tale written by Johann Karl Christoph Nachtigal and published in 1800 under the name Otmar. A goatherd looking for a lost goat finds men drinking in the woods, drinks their wine, falls asleep, and wakes twenty years later.
- Headless horsemen. Headless riders turn up in German, Irish and Scandinavian legend, and in poems such as Robert Burns’s “Tam o’ Shanter” (1790) and Gottfried August Bürger’s Der Wilde Jäger (1778), later translated as The Wild Huntsman. One influential version is among Johann Karl August Musäus’s retellings of German folk tales, Volksmärchen der Deutschen (1782–86).
- A real war zone. During the Revolution, after the Battle of White Plains in October 1776, Westchester County became a no man’s land between the armies, the “Neutral Ground.” Raiders and soldiers, including German Hessians, passed through the area. A Hessian ghost made sense there. The story itself is set around 1790, when those war stories were still fresh.
- Real people, maybe. Irving may have taken the name Ichabod Crane from an army captain he met in 1814. The schoolmaster himself may have been partly modeled on Jesse Merwin, a teacher in Kinderhook, New York, where Irving spent several months in 1809. Both ideas are likely but not proved. The Van Tassel farmhouse may have been based on Philipsburg Manor, near Sleepy Hollow.
The story itself says war stories grow with time: “Just sufficient time had elapsed to enable each storyteller to dress up his tale with a little becoming fiction, and in the indistinctness of his recollection to make himself the hero of every exploit.” That line describes Irving’s own method, too.
Why Irving Matters
An early American short story
Britannica says “Rip Van Winkle” and “Sleepy Hollow” “have been called the first American short stories.” Whether or not they were the very first, they were among the first American tales to win readers at home and in Europe, and they are still read two centuries later.
American places
Irving set European-style legends firmly in American places. He showed that the Hudson Valley could be as haunted and as storied as the Rhine. Writers after him set their stories in their own corners of the country.
A writing life
Britannica calls Irving the “first American man of letters.” The Sketch Book did so well that he could live by his pen, and he is often credited as the first American to make writing alone his living. He encouraged younger writers; Edgar Allan Poe sent him stories and asked for his comments.
Names that stuck
“Knickerbocker” still means a New Yorker. A “Rip Van Winkle” is anyone badly out of date. In 1996 the village of North Tarrytown renamed itself Sleepy Hollow, and the Headless Horseman has been filmed many times, including a 1949 Disney cartoon.
From Irving to O. Henry. Irving’s tales came out in installments, like a magazine. Eighty years later, O. Henry wrote for weekly newspapers. Compare their endings: O. Henry’s twist closes the case, while Irving’s ending leaves it open.
Period Attitudes
These stories were written around 1819 and look back to the 1770s through the 1790s. Reading them well means noticing the attitudes of both times.
- Slavery in the background. “Sleepy Hollow” is set around 1790, when slavery was legal in New York. A 1799 state law for gradual abolition freed no one who was already enslaved, and the last enslaved New Yorkers were not freed until July 4, 1827. Philipsburg Manor, the estate that may have inspired the Van Tassel farm, was largely run by enslaved Africans. The story never mentions any of this.
- Racist caricature. The few Black characters in “Sleepy Hollow,” a messenger, a fiddler and onlookers at the party, are background figures described in mocking, racist terms. Those descriptions were common in white American writing of the time and are hurtful now. We have not quoted them. Ask who the story treats as a full person and who it treats as scenery.
- Native Americans as legend. Both tales mention Native Americans only as figures in ghost stories, old spells and wild tales of the past, never as living neighbors. A postscript to “Rip Van Winkle” repeats stereotyped “Indian traditions” that we do not reprint.
- Wives and women. Dame Van Winkle exists mostly as a joke about a nagging wife, and the story treats her death as good news for Rip. Katrina is described as a prize to be won along with her father’s farm, and we never learn what she thinks. Notice that the narrator says he does not know what she told Ichabod.
- Ichabod as a type. Ichabod is a comic caricature of a New England “Yankee”: skinny, greedy and gullible. Dutch New Yorkers and New Englanders had a long rivalry, and the story takes the Dutch side. It also mocks Hans Van Ripper, who burns Ichabod’s books and decides “he never knew any good come of this same reading and writing.”
Ghost or Joke?
Read the Storyteller’s Wink
Eight rounds, four from each story. Each round asks a question and gives three real details from the story. Choose the one that answers it. A right pick is marked ✓ Right; a wrong pick is marked ✗ Try again, and you can choose again. Your score counts first tries.
Answer key
- Rip keeps tasting the “excellent Hollands”
- The flagon “has addled my poor head sadly!”
- “I have even talked with Rip Van Winkle myself”
- King George on the inn sign is now “GENERAL WASHINGTON.”
- Brom tells of racing the Hessian to the church bridge
- His hat, and beside it “a spattered pumpkin”
- He laughs whenever the pumpkin comes up
- “I don’t believe one-half of it myself.”
Quiz
The Washington Irving Quiz
Choose one answer per question. Your pick is marked ✓ if it is right or ✗ if it is not, the right answer is marked ✓, and a short explanation follows. Your score appears at the end.
Answer key
- George Washington
- Newspaper notices that an old historian had vanished from his hotel
- Geoffrey Crayon
- At his sister’s home in Birmingham, England
- Twenty years
- King George now stands for General Washington
- Hendrick Hudson and the crew of the Half-moon
- He believes Cotton Mather’s book on witchcraft
- Turning it into cash to buy wild land
- Ichabod’s hat and a spattered pumpkin
- He became a lawyer, a politician and a judge
- An outer story around the main story
- Unbelievable events told as if true
- They have been called the first American short stories
Connecting the Stories
For class or for your own journal. Use evidence from both stories.
- Rip and Ichabod both leave home and come back changed, or do not come back at all. What does each story suggest about outsiders and the communities they live in?
- Both stories use the American Revolution in the background. Find one detail in each that shows the war. Why might Irving keep the war offstage?
- Both tales end with what the locals still say “to this day.” Why end with gossip instead of a final answer?
- Rank the two stories from most to least believable. Does the frame narrator make each one more believable, or less?
- The period attitudes note points out who is left out of these stories. Retell one scene from the point of view of Dame Van Winkle, Katrina or another background character.
- Write a local legend of about 300 words about a real place you know. Tell it through a narrator who is not quite sure it is true, and plant one detail that might explain the mystery.
Sources and Credits
- Washington Irving, “Rip Van Winkle” and “The Legend of Sleepy Hollow,” in The Sketch Book of Geoffrey Crayon, Gent., Project Gutenberg eBook #2048 (gutenberg.org/ebooks/2048), including the note after “Rip Van Winkle” and the postscript to “Sleepy Hollow.”
- Washington Irving, The Legend of Sleepy Hollow, Project Gutenberg eBook #41 (gutenberg.org/ebooks/41).
- Encyclopaedia Britannica, “Washington Irving” (life dates, “first American man of letters,” the two tales called the first American short stories and “Americanized versions of German folktales,” and living by his pen).
- Wikipedia, “Washington Irving” (family, the 1798 stay in Tarrytown, Jonathan Oldstyle, the bar exam, Salmagundi, the Knickerbocker hoax and December 6, 1809, the move to England, Birmingham, John Murray, the return on May 21, 1832, Sunnyside, Spain and Poe), “Rip Van Winkle” (the Catskills quotation and “Peter Klaus”), “The Sketch Book of Geoffrey Crayon, Gent.” (installments, C. S. Van Winkle, June 23, 1819), “The Legend of Sleepy Hollow” (setting around 1790, headless-horseman sources, Musäus, the Neutral Ground, Ichabod’s possible models, the 1949 film), “Diedrich Knickerbocker,” “A History of New York,” “Peter Klaus,” “Frame story,” “Tall tale,” “Philipsburg Manor House” and “History of slavery in New York (state)” (the 1799 law and July 4, 1827).
- German Wikipedia, “Johann Karl August Musäus” (Volksmärchen der Deutschen, five volumes, 1782–1786).
- The March 15, 1820 date for “The Legend of Sleepy Hollow” in the sixth installment is also given by the biographer Brian Jay Jones and by blog posts of the New-York Historical Society and the New York Public Library.
- Summaries are our own paraphrases. Every quotation from the stories was checked against the Project Gutenberg texts above.
- Art: the Catskills ninepins and church-bridge illustrations and the preview image are original artwork made for Jugami.