Rip Van Winkle
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40 free Rip Van Winkle trivia questions with answers — literature quiz, new questions added Oct 2026.
Rip Van Winkle is one of the first great short stories written in the United States, and almost everyone knows its outline: a good-natured idler wanders into the mountains, shares a drink with some very odd strangers, and wakes to find that everything has moved on without him. The details are where a quiz gets interesting. These multiple-choice questions work as a reading and comprehension check on the story itself: who is who in the village, what Rip finds when he walks home, how the narrator describes his marriage, and which lines readers still quote. A second strand covers the author's life, the folk tales behind the plot, and the plays, films and games that have borrowed the sleeper's name. It suits students revising the text, teachers who want a ready-made quiz to print, and anyone curious how much of the tale they really remember. Every answer comes with a short explanation, so you learn the story as you play.
30 of 40 questions with answers and explanations. Play the quiz
Q 01In Rip Van Winkle, how long does Rip sleep after wandering into the mountains with his dog and gun?
Twenty years
Twenty years pass in what feels to Rip like one night. He walks home to find his house in ruins and nobody in the village who knows his face.
Q 02Which New York-born author wrote Rip Van Winkle in England after his family firm went bankrupt?
Washington Irving
Washington Irving became one of the first writers from the United States to win acclaim in Europe. Lord Byron said he knew the collection the tale appeared in by heart.
Q 03Which conflict does Rip Van Winkle sleep through after wandering off from his colonial village?
The American Revolution
The American Revolution is fought and won while Rip sleeps. One old friend marched off to the war and never came back, and the loafers outside the inn now argue hotly about rights and liberty.
Q 04In Rip Van Winkle, which game do the silent strangers play, its rolling balls echoing like thunder?
Ninepins
Ninepins is the game, played in eerie silence by grave-faced men in antique Dutch dress. Villagers later say every summer thunderstorm is the ghostly crew at play again.
Q 05In Rip Van Winkle, what is the name of Rip's dog, blamed by Dame Van Winkle for leading him astray?
Wolf
Wolf is as henpecked as his master, slinking off at the wave of a broomstick. After the long sleep, a snarling dog that looks just like him no longer knows Rip.
Q 06Which mountain range is the setting of Rip Van Winkle, though its author had never set foot there?
The Catskills
The Catskills are called fairy mountains in the tale, their colors shifting so reliably that local wives read them like barometers. A sculpture of Rip now sits near the summit of Hunter Mountain.
Q 07In Rip Van Winkle, what does a bewildered Rip discover has grown a foot long as he walks home?
His beard
His beard is the first proof of how long he has slept. Rip only notices it when he copies the strangers he passes, who all stare at him and stroke their chins.
Q 08In Rip Van Winkle, which monarch's red-coated portrait hangs on the inn sign before Rip's sleep?
King George III
King George III beams from the sign in a red coat, holding a scepter. Rip wakes to find the same face repainted in blue and buff, with a sword and a new name underneath.
Q 09Which other famous tale shares its original story collection with Rip Van Winkle?
The Legend of Sleepy Hollow
The Legend of Sleepy Hollow joined it in The Sketch Book, a mix of 34 essays and stories. Both tales are presented as the work of the same fictional Dutch historian.
Q 10In Rip Van Winkle, the strangers are the ghostly crew of which explorer, who sailed for the Dutch?
Henry Hudson
Henry Hudson is said to return with his crew to keep watch over the river that bears his name. The village's oldest man swears his own father once saw them.
Q 11In Rip Van Winkle, the narrator calls Rip's great flaw an insuperable aversion to all kinds of what?
Profitable labor
Profitable labor is the one thing Rip cannot face. He will fish all day without a nibble or help build a neighbor's stone fence, yet his own fields go to weeds.
Q 12In Rip Van Winkle, which animals does Rip love to shoot on his long rambles through the mountains?
Squirrels
Squirrels are his usual quarry, and the hills echo with his gun all day. The chase carries him, without his noticing, to one of the highest points of the range.
Q 13In Rip Van Winkle, what does Rip find beside him when he wakes, in place of his well-oiled gun?
A rusty firelock
Q 21In Rip Van Winkle, what is the first name of Rip's grown daughter, who takes him into her home?
Judith
Judith arrives carrying a baby she calls Rip, and her voice stirs the old man's memory. She was a little girl when her father walked off with his gun.
Q 22In Rip Van Winkle, which innkeeper rarely speaks but shows his opinions by how he puffs his pipe?
Nicholas Vedder
Nicholas Vedder sits at the inn door all day, shifting with the shade so exactly that neighbors tell the time by him. Angry, he puffs hard; pleased, he breathes out slow, placid clouds.
Q 23In Rip Van Winkle, which rickety new building has replaced the quiet Dutch inn when Rip returns?
The Union Hotel
A rusty firelock, its lock falling off and its stock worm-eaten, makes Rip suspect the strangers drugged him and stole his own weapon. The narrator later calls it simply his rusty fowling-piece.
Q 14Back home in Rip Van Winkle, which unfamiliar flag does Rip see flying from a tall bare pole?
The Stars and Stripes
The Stars and Stripes flutters where the inn's great shade tree once stood. Rip also puzzles over something on top of the pole that looks to him like a red nightcap.
Q 15In Rip Van Winkle, whom does Rip see leaning against a tree, a precise copy of his younger self?
His own son
His own son, also called Rip, has grown into the same ragged idler. The sight so rattles the old man that he doubts his own identity and cannot say who he is.
Q 16What does the crowd in Rip Van Winkle call Rip when he declares himself a loyal subject of the King?
A Tory
A Tory is the worst thing a man can be called in this crowd. The mob also cries spy and wants the old man hustled away, until a self-important fellow in a cocked hat restores order.
Q 17In Rip Van Winkle, which public event is under way outside the tavern when Rip returns home?
An election
An election has the tavern in uproar, and strangers demand to know which side Rip voted on. He can only stare, having never heard of either party.
Q 18In Rip Van Winkle, the ghostly strangers once sailed aboard which Dutch East India Company ship?
Half Moon
Half Moon, or Halve Maen, was the small ship that entered what is now New York Harbor in 1609. The tale has her long-dead crew return to the mountains to drink and play.
Q 19Which Nintendo game honors Rip Van Winkle with a constantly dozing fish enemy named Rip Van Fish?
Super Mario World
Super Mario World fills its water levels with Rip Van Fish, which snooze until Mario swims too close and then wake up and chase him.
Q 20Which TV anthology series aired The Rip Van Winkle Caper, about gold thieves asleep for a century?
The Twilight Zone
The Twilight Zone aired the episode in 1961, written by Rod Serling. The thieves wake to find their gold worthless, because it can now be manufactured.
The Union Hotel, kept by Jonathan Doolittle, is a large wooden pile with gaping windows mended with old hats. Rip later tells his story there to every stranger who arrives.
Q 24In Rip Van Winkle, Dame Van Winkle dies after bursting a blood vessel while raging at which visitor?
A peddler
A peddler from New England is the last target of her temper. The news comes to Rip as a drop of comfort, since he had walked home dreading her.
Q 25In Rip Van Winkle, the strangers' drink tastes of excellent Hollands, an old name for which spirit?
Gin
Gin of the Dutch kind, also called jenever, was long sold in English as Hollands. Rip keeps going back to the flagon until his eyes swim and he sinks into a deep sleep.
Q 26In Rip Van Winkle, what has schoolmaster Derrick Van Bummel become by the time Rip wakes up?
A congressman
A congressman is what the dapper little teacher has become, after serving as a great militia general. Rip, who knew him as a reader of long words, can make no sense of the news.
Q 27Rip Van Winkle is presented as a tale found among the papers of which fictional historian?
Diedrich Knickerbocker
Diedrich Knickerbocker was first invented for a hoax: newspaper notices reported the old historian missing from his lodgings, to drum up interest in a satirical history of New York.
Q 28The author of Rip Van Winkle wrote it in one night at his sister's home in which English city?
Birmingham
Birmingham was home to his merchant brother-in-law, and a nostalgic chat between the two set the story off. He read the first draft to the family over breakfast.
Q 29Rip Van Winkle is widely thought to draw on Peter Klaus, a goatherd folk tale from which country?
Germany
Germany gave the tale its skeleton: goatherd Peter Klaus drinks wine with strangers in the woods and wakes long afterward. Johann Nachtigal published it in 1800 under the alias Otmar.
Q 30At the end of Rip Van Winkle, which form of despotism is Rip happiest to have slept his way out of?
Petticoat government
Petticoat government, meaning rule by his wife, is the only tyranny Rip ever felt. The change of states and empires hardly touches him; freedom from her lectures does.