The Legend of Sleepy Hollow
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50 free The Legend of Sleepy Hollow trivia questions with answers — literature quiz, new questions added Oct 2026.
Washington Irving's The Legend of Sleepy Hollow has been spooking readers for two centuries. A lanky, superstitious schoolmaster named Ichabod Crane sets his heart on the daughter of a rich farmer, crosses the local hero Brom Bones, and rides home one night with something terrible at his heels. It is one of the first American short stories to become famous around the world, and it is funnier than most people remember. This quiz follows the tale from the drowsy valley of the opening pages to the mystery of the last ones. Expect questions on Ichabod, Katrina Van Tassel and Brom Bones, the feast and the ghost stories at the Van Tassel farm, the midnight chase, and the clues Irving leaves about what really happened. A smaller group covers the author's life and the best-known screen versions, from the Disney cartoon to Tim Burton's film. Students can use it as a comprehension check after reading, and teachers get a ready-made multiple choice set for middle school and up. The opening questions are the gentlest, later ones reward close readers, and every answer comes with a short explanation.
30 of 50 questions with answers and explanations. Play the quiz
Q 01In The Legend of Sleepy Hollow, what is found smashed beside Ichabod Crane's hat the morning after he vanishes?
A pumpkin
A pumpkin lies in pieces by the brook, Irving's sly hint that no real ghost was involved. The water was searched, but the schoolmaster's body was never discovered.
Q 02Washington Irving wrote The Legend of Sleepy Hollow in which country, where he had gone to rescue the family firm?
England
England was Irving's home when he wrote this very American tale. He had sailed over in 1815 for the family business, which went bankrupt, and he turned to writing for a living.
Q 03In The Legend of Sleepy Hollow, what does the Headless Horseman do just as Ichabod Crane thinks he has reached safety?
Hurls his head at him
The rider rises in his stirrups and hurls his head at him, a missile Ichabod tries too late to dodge. It strikes his skull with a tremendous crash and tumbles him into the dust.
Q 04Which actor plays an eccentric, science-minded Ichabod Crane in Tim Burton's 1999 horror film Sleepy Hollow?
Johnny Depp
Johnny Depp described his Crane as a very delicate, fragile person. Burton sends him to investigate a string of beheadings, a far bloodier plot than Irving's comic tale.
Q 05In Sleepy Hollow lore, the Headless Horseman is said to be the ghost of what kind of Revolutionary War soldier?
A Hessian trooper
A Hessian trooper is the ghost named at every fireside in the valley. His body lies in the churchyard, and he gallops out each night in search of his missing head, hurrying back before daybreak.
Q 06In Disney's 1949 cartoon of The Legend of Sleepy Hollow, Brom Bones says the Headless Horseman rides on which night?
Halloween
Halloween is the night Brom names, claiming the ghost hunts for a living head to replace his own. Irving's original story never mentions the holiday at all.
Q 07In The Legend of Sleepy Hollow, wives named nearby Tarry Town because their husbands lingered where on market days?
The village tavern
The village tavern kept the men so long that, Irving jokes, the good housewives named the whole place for their tarrying. His narrator slyly adds that he does not vouch for the fact.
Q 08Irving writes that Sleepy Hollow's lanky Ichabod Crane, clothes fluttering on a windy hill, could be taken for what?
A scarecrow
A scarecrow eloped from a cornfield is Irving's image for the gangly teacher. He adds that Crane's small head sat on his spindle neck like a weathercock telling which way the wind blew.
Q 09In Sleepy Hollow, which animal does Brom Bones teach to whine and introduce to Katrina as Ichabod Crane's rival?
A dog
A dog, a scoundrel in Irving's words, was taught to whine in the most ludicrous manner so Brom could ridicule the teacher in front of Katrina. Ichabod had wisely refused to fight him.
Q 10Which nickname for New York City did Sleepy Hollow author Washington Irving first use in his 1807 magazine Salmagundi?
Gotham
Gotham, an Anglo-Saxon word meaning Goat's Town, appeared in the seventeenth issue of Salmagundi. Irving and his friends used the magazine to lampoon New York's culture and politics.
Q 11In The Legend of Sleepy Hollow, what is the name of the broken-down plow horse Ichabod Crane borrows for the party?
Gunpowder
Gunpowder had outlived almost everything but his viciousness. Gaunt and shaggy, with one eye missing its pupil, he still had more lurking devil in him than any young filly in the country.
Q 12Ichabod Crane of Sleepy Hollow is a native of which state, said to send forth legions of country schoolmasters?
Connecticut
Connecticut, Irving writes, supplies the Union with pioneers for the mind as well as for the forest. Crane thrills his hosts with tales of the omens and witchcraft of his home state.
Q 13In The Legend of Sleepy Hollow, Ichabod Crane firmly believes a witchcraft history written by which colonial minister?
Q 21When Ichabod Crane first sees the Headless Horseman against the sky in Sleepy Hollow, where is the rider's head?
On his saddle pommel
On his saddle pommel sat the head that should have rested on his shoulders, and the sight turned Ichabod's terror to desperation. He rained kicks and blows on his old horse to give the rider the slip.
Q 22In The Legend of Sleepy Hollow, which landmark does the fleeing Ichabod Crane believe he must reach to be safe?
The church bridge
The church bridge was where the ghost had vanished in Brom Bones's tale, so Ichabod expects the same. The spot later inspired such superstitious awe that, Irving suggests, the road was altered to avoid it.
Q 23At the Van Tassel party in Sleepy Hollow, Brom Bones boasts he once raced the Headless Horseman for what prize?
Cotton Mather
Cotton Mather was Crane's favorite author. He would lie in the clover by the brook poring over the book's direful tales until dusk, then walk home startled by every sound.
Q 14Which horse, a creature full of mettle and mischief, does Brom Bones ride to the Van Tassel party in Sleepy Hollow?
Daredevil
Daredevil was a horse no one but Brom could manage. He preferred vicious animals that kept the rider in constant risk of his neck, and thought a well-broken horse unworthy of a lad of spirit.
Q 15In The Legend of Sleepy Hollow, what is said to have carried away the Headless Horseman's head in a nameless battle?
A cannonball
A cannonball took it off, and the ghost is said to ride to the scene of battle each night to look for it. Real records note a soldier beheaded that way at White Plains in 1776.
Q 16In The Legend of Sleepy Hollow, a rider on a half-broken colt invites Ichabod Crane to what kind of party?
A quilting frolic
A quilting frolic at the Van Tassel farm was the invitation, and the school was turned loose an hour early. Ichabod then spent an extra half hour grooming with a bit of broken looking-glass.
Q 17On dark walks home in Sleepy Hollow, what does a frightened Ichabod Crane do to drive away evil spirits?
Sings psalm tunes
He sings psalm tunes, and villagers sitting by their doors were often filled with awe at his nasal melody floating from a distant hill. Giving music lessons was also his side job.
Q 18How does Brom Bones look whenever the tale of Ichabod Crane's disappearance is told in Sleepy Hollow?
Exceedingly knowing
Exceedingly knowing is Irving's phrase, and it led some to suspect Brom knew more about the matter than he chose to tell. He had led Katrina to the altar soon after his rival vanished.
Q 19An old farmer back from New York reports that Ichabod Crane survived Sleepy Hollow and ended up as what?
A court justice
A court justice was his final post, on what Irving calls the Ten Pound Court. He had moved away, kept school while studying law, been admitted to the bar, turned politician and written for the newspapers.
Q 20After Ichabod Crane vanishes from Sleepy Hollow, what does farmer Hans Van Ripper do with his books of witchcraft?
Burns them
He burns them, along with Ichabod's blotted attempts at verses for Katrina. Van Ripper then resolved to send his children to school no more, saying no good ever came of reading and writing.
A bowl of punch
A bowl of punch was the stake, and Brom swears his horse was winning until the ghost bolted and vanished in a flash of fire. He says it happened as he rode home from Sing Sing.
Q 24In a Sleepy Hollow ghost tale, the Headless Horseman throws old Brouwer into a brook after turning into what?
A skeleton
A skeleton is what he became before springing away over the treetops with a clap of thunder. Old Brouwer had been a most heretical disbeliever in ghosts until that ride.
Q 25Irving says lank Ichabod Crane of Sleepy Hollow, a huge feeder, has the dilating powers of which animal?
An anaconda
An anaconda is the comparison, and the feast at the Van Tassel farm shows why. Irving says Ichabod's spirits rose with eating as some men's do with drink.
Q 26How does the poorly paid schoolmaster Ichabod Crane keep a roof over his head in The Legend of Sleepy Hollow?
Lodging with pupils' families
Lodging with pupils' families a week at a time, he went the rounds of the farms with all his worldly effects tied up in a handkerchief. He made himself useful with chores and by minding the babies.
Q 27Which 'golden maxim' does Irving say schoolmaster Ichabod Crane ever bore in mind in his Sleepy Hollow classroom?
Spare the rod, spoil the child
Spare the rod, spoil the child was his rule, and Irving dryly notes that Crane's scholars certainly were not spoiled. He went easy on the weak and gave the tough ones a double portion.
Q 28Which fried treat heads Irving's list of Dutch cakes on the Van Tassel tea table in The Legend of Sleepy Hollow?
The doughnut
The doughnut, which Irving calls doughty, comes first, followed by the tender oly koek and the crisp and crumbling cruller. Such cakes, he says, were known only to experienced Dutch housewives.
Q 29Irving compares Ichabod Crane's clattering dancing at the Sleepy Hollow party to which saint, the patron of the dance?
St. Vitus
St. Vitus himself seemed to be figuring before you in person, Irving writes, with not a limb or fibre of the lanky teacher idle. Katrina was his partner while Brom Bones sat brooding in a corner.
Q 30What does Ichabod Crane daydream of doing with the Van Tassel farm once he has married Katrina in Sleepy Hollow?
Selling it for cash
Selling it for cash was his plan, with the money sunk into tracts of wild land. He pictured Katrina and a wagonload of children setting out for Kentucky, Tennessee or the Lord knows where.