Washington Irving
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50 free Washington Irving trivia questions with answers — literature quiz, new questions added Oct 2026.
Washington Irving was one of the first American writers to win acclaim in Europe, and two of his tales have never gone out of print. Most people can picture the sleeper who wakes to a changed world and the schoolmaster fleeing a headless rider, even if they have never read a page of the originals. This quiz covers the stories themselves, with questions on their plots, characters and settings, alongside the life behind them: a New York childhood, a long spell abroad, a diplomatic career, and friendships with the leading writers of the age. It also looks at the words, nicknames and holiday customs he left behind, some of which you probably use without knowing where they came from. It suits students revising his short stories, teachers after a ready-made quiz to print, and anyone who enjoys American literature. Every answer comes with a short explanation, so you pick up the story behind each fact as you play.
30 of 50 questions with answers and explanations. Play the quiz
Q 01Which nickname did Washington Irving give New York City in an 1807 issue of his satirical magazine?
Gotham
Gotham, an Anglo-Saxon name meaning Goat's Town, came from an English village whose people were proverbially foolish. The joke outlived the magazine by two centuries.
Q 02Which New York sports team is named after a fictional Dutch historian invented by Washington Irving in 1809?
Knicks
The Knicks are short for Knickerbockers, after Diedrich Knickerbocker, the crusty narrator of Irving's comic A History of New York. His surname became a byword for New Yorkers.
Q 03Which lanky schoolmaster is chased by the Headless Horseman in Washington Irving's The Legend of Sleepy Hollow?
Ichabod Crane
Ichabod Crane is never seen in the valley again after the midnight chase. The tale hints that a rival for a rich farmer's daughter, not a ghost, was the rider.
Q 04In Washington Irving's Rip Van Winkle, how long does Rip sleep after drinking with strangers in the mountains?
Twenty years
Twenty years slip by in what feels to Rip like a single night. He walks home with a foot-long grey beard to a village where nobody knows his face.
Q 05Which false belief about medieval Europeans was spread by Washington Irving's 1828 biography of Christopher Columbus?
They thought Earth was flat
They thought Earth was flat only in Irving's largely fictional scene of scholars doubting Columbus. The real dispute in the 1490s was over the planet's size.
Q 06Which English novelist was romantically interested in Washington Irving, as he learned from a playwright friend?
Mary Shelley
Mary Shelley, the author of Frankenstein, had her interest relayed to Irving by the playwright John Howard Payne. Irving never followed it up.
Q 07Which phrase about money is Washington Irving credited with coining in his tale The Creole Village?
The almighty dollar
The almighty dollar was Irving's mocking name for the object of universal devotion he saw across America, with banks as its pious shrines.
Q 08Which director turned Washington Irving's The Legend of Sleepy Hollow into a 1999 horror film led by Johnny Depp?
Tim Burton
Tim Burton recast the timid schoolmaster as a city police constable sent upstate to investigate a string of beheadings. The film won the Oscar for Best Art Direction.
Q 09In 1940, Washington Irving's portrait opened a series honouring American authors on which everyday item?
A postage stamp
A postage stamp worth one cent carried Irving's face, the first in a set of writers that went on to include Mark Twain and Louisa May Alcott.
Q 10Which conflict does Rip Van Winkle sleep through in Washington Irving's famous tale?
The American Revolution
The American Revolution comes and goes while Rip sleeps. Asked how he voted, he alarms the crowd by declaring himself a loyal subject of King George III.
Q 11Which English novelist credited Washington Irving's sketches of a manor-house Christmas as an influence on his own?
Charles Dickens
Charles Dickens named Irving as an influence on his Christmas writings, A Christmas Carol among them. The two struck up a friendly correspondence before he toured America in 1842.
Q 12Which English poet said he knew Washington Irving's The Sketch Book by heart and wept over one of its tales?
Lord Byron
Lord Byron claimed the sentimental sketch The Broken Heart had made him weep. The collection was among the first American books to be widely read in Britain and Europe.
Q 13Which Scottish novelist did Washington Irving visit in 1817, beginning a friendship that won him a top London publisher?
Q 21In Washington Irving's The Legend of Sleepy Hollow, what lies beside the vanished schoolmaster's hat the next morning?
A pumpkin
A pumpkin, found smashed beside the brook, suggests the goblin's flung head was nothing of the kind. The schoolmaster's rival burst into a hearty laugh whenever it was mentioned.
Q 22Which burly rival of the schoolmaster in Washington Irving's The Legend of Sleepy Hollow rides a horse named Daredevil?
Brom Bones
Brom Bones leads the heiress to the altar soon after his rival disappears. He looks exceedingly knowing whenever the tale of the midnight chase is told.
Q 23In Washington Irving's The Legend of Sleepy Hollow, the Headless Horseman is said to be the ghost of which soldier?
A Hessian trooper
Walter Scott
Walter Scott talked his own publisher, John Murray, into taking on The Sketch Book. In gratitude, Irving dedicated the English editions to him.
Q 14Which American writer called Washington Irving much overrated in 1838, yet sought his comments on his own Gothic tales?
Edgar Allan Poe
Edgar Allan Poe granted Irving a pioneer's credit but thought the writing itself overpraised. He still asked for Irving's opinion of The Fall of the House of Usher.
Q 15Which American vice president founded the newspaper that printed Washington Irving's first letters in 1802?
Aaron Burr
Aaron Burr liked the young satirist's letters enough to send clippings to his daughter Theodosia. Irving's brother Peter edited the paper.
Q 16Which fur magnate persuaded Washington Irving to write a history of his trading colony on the Oregon coast?
John Jacob Astor
John Jacob Astor later named Irving in his will as first chairman of the Astor Library, a forerunner of the New York Public Library.
Q 17Washington Irving's A Tour on the Prairies recounts his 1832 ride through Indian Territory, now which state?
Oklahoma
Oklahoma was the frontier Irving crossed with a federal commissioner on a surveying expedition. The book was his first written and published in America since 1809.
Q 18Washington Irving trained as what before turning to writing, barely passing the qualifying examination in 1806?
A lawyer
A lawyer in name only, Irving admitted he was a poor student and scraped through the bar. Within months he was lampooning the city's politics in print instead.
Q 19A friendship struck in Rome in 1805 nearly persuaded Washington Irving to take up which career?
Painter
Painter was nearly Irving's calling after he befriended the American artist Washington Allston in Rome. He later wrote that his lot in life was differently cast.
Q 20An outbreak of which disease in 1798 sent the teenage Washington Irving upriver to the valley he later made famous?
Yellow fever
Yellow fever led the family to send him to stay with a friend upriver, where he first met the Dutch customs and local ghost tales he later used.
A Hessian trooper, one of the German soldiers hired by the British, lost his head to a cannonball in some nameless battle and rides out nightly in search of it.
Q 24From which state does the schoolmaster hero of Washington Irving's The Legend of Sleepy Hollow come to teach?
Connecticut
Connecticut, the narrator jokes, supplies the Union with country schoolmasters as readily as frontier woodsmen. The newcomer is an outsider among the valley's old Dutch families.
Q 25Which game are the strange bearded men playing when Rip finds them in Washington Irving's Rip Van Winkle?
Ninepins
Ninepins explains the thunder, the old villagers decide: whenever it rumbles over the mountains, the ghostly crew must be bowling again.
Q 26What is the name of Rip's faithful dog, his companion on the mountain in Washington Irving's Rip Van Winkle?
Wolf
Wolf is as henpecked as his master, and the pair slip away to the woods together for peace. When Rip wakes, the dog is nowhere to be found.
Q 27In Washington Irving's The Devil and Tom Walker, which pirate's buried treasure does the Devil offer to Tom?
Captain Kidd
Captain Kidd, in the tale's legend, buried his gold near a swamp outside Boston with the Devil as its guardian, then was hanged before he could come back for it.
Q 28In Washington Irving's The Devil and Tom Walker, which trade does Tom take up after refusing to deal in slaves?
A moneylender
A moneylender is what Tom becomes, so miserly in his new wealth that he buys a grand coach and half-starves the horses that pull it.
Q 29In Washington Irving's The Adventure of the German Student, what had killed the hero's mysterious lover a day earlier?
The guillotine
The guillotine had taken her head, as the hero learns when a policeman undoes the black band at her neck. Irving heard the grisly anecdote from the Irish poet Thomas Moore.
Q 30Which English manor, home of the family in his Christmas sketches, titles Washington Irving's 1822 book?
Bracebridge Hall
Bracebridge Hall let Irving revisit the hospitable family of his Christmas sketches in more than 50 loosely connected tales and essays.