Winesburg, Ohio
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40 free Winesburg, Ohio trivia questions with answers — literature quiz, new questions added Oct 2026.
Sherwood Anderson's Winesburg, Ohio came out in 1919 and changed what American fiction could do with a small town. Instead of one plot it offers a string of linked tales, each built around a single resident whose private longing has bent a life out of shape, with the young reporter George Willard drifting through as listener and witness. The prose is plain, the feeling is not, and writers have been borrowing from it ever since. This quiz follows the book the way readers meet it. There are questions on the stories students are most often set, including Loneliness, Paper Pills, Respectability, Mother, The Teacher and Sophistication, along with Hands, Godliness, Adventure and The Strength of God. You will be asked about Enoch Robinson's room, Doctor Reefy's pockets, Wash Williams's grudge, Elizabeth Willard's secret plans, Kate Swift's advice and the evening George spends with Helen White. A final group covers Anderson himself: where the town came from, how the tales were written and published, and the writers the book went on to influence. It suits literature students revising for a class, book clubs working through the collection, and anyone who read it years ago and wants to see what has stayed with them. Every answer comes with a short explanation tied to the text.
30 of 40 questions with answers and explanations. Play the quiz
Q 01Sherwood Anderson, author of Winesburg, Ohio, died in Panama after accidentally swallowing which small object?
A toothpick
A toothpick, an autopsy found, had pierced his insides and caused fatal peritonitis; he was taken ill on a cruise to South America, aged 64.
Q 02In Loneliness, what does Enoch Robinson fill his locked New York room with once he stops inviting friends in?
Shadow people
Shadow people, about two dozen figures of his own fancy, share the room and let him talk last and best, among them a woman with a sword and an old man trailed by a dog.
Q 03Wash Williams, the filthy woman-hater of Respectability, holds which job at the Winesburg railroad station?
Telegraph operator
Telegraph operator was a trade he had once been called the best at in the whole state, before his marriage collapsed and he was tucked away in the obscure Winesburg office.
Q 04In The Strength of God, what does Reverend Curtis Hartman smash with his fist after watching Kate Swift pray?
A church window
A church window in the bell tower was his peephole into her bedroom, and he hurries off bleeding to tell George Willard that God has appeared to him in her.
Q 05Paper Pills likens Doctor Reefy's courtship to which gnarled fruit, left on Winesburg's trees by the pickers?
Apples
Apples too twisted to ship to the city hold all their sweetness in one small spot, the tale says, and they look like the knuckles of the doctor's hands.
Q 06Sophistication opens on the day of which annual event, which has packed Winesburg's Main Street with country people?
The county fair
The county fair is over by the time George Willard and Helen White climb to its empty grandstand, where they sit in the dark and hardly speak.
Q 07In Adventure, what does lonely Alice Hindman do on impulse before crawling home in shame?
She runs outside naked
She runs outside naked into the rain and calls to a passing man, who proves old and somewhat deaf; she ends the tale facing the fact that many people live and die alone.
Q 08Tom and Elizabeth Willard run which failing Winesburg business, which once belonged to Elizabeth's father?
A hotel
A hotel called the New Willard House, it is still recorded in Elizabeth's name, and its shabbiness comes to stand for her own defeated life.
Q 09Which novelist, whose early career Sherwood Anderson helped launch, mocked him in the parody The Torrents of Spring?
Ernest Hemingway
Ernest Hemingway aimed the parody at Dark Laughter, the only bestseller Anderson ever had, which had come out the year before.
Q 10Enoch Robinson of Loneliness leaves his mother's farm near Winesburg for New York hoping to become what?
A painter
A painter was the plan: he studied French and went to an art school, meaning to finish his training in Paris, but nothing ever turned out for him.
Q 11George Willard is the young reporter on which Winesburg newspaper, a job his father Tom arranged for him?
The Eagle
The Eagle, in full the Winesburg Eagle, is a weekly owned and edited by Will Henderson, and the post puts George where half the town comes to confide in him.
Q 12Which story comes last of all in Winesburg, Ohio?
Departure
Departure ends with George lost in small memories in his seat, and when he looks up the town has slipped out of sight for good.
Q 13Sherwood Anderson wrote the Winesburg tales in a Chicago rooming house while earning his living in which trade?
Advertising
Advertising paid the bills: he said the tales came to him on evenings in his room, and sometimes during the day at the office where he wrote copy.
Q 21In Mother, which weapon does Elizabeth Willard take from a cloth bag, meaning to stab her husband Tom?
Sewing scissors
Sewing scissors in hand, she plans to make herself up from a box left by stranded players and stride downstairs like a tigress, but her strength fails and the plan dies.
Q 22In Mother, Elizabeth Willard watches the baker Abner Groff carry on a long feud with which animal?
A cat
A cat belonging to the druggist keeps slipping into the bakery, and the baker's useless rages come to seem to her a rehearsal of her own life.
Q 23In Death, where has Elizabeth Willard kept the eight hundred dollars her father gave her to escape Winesburg?
Behind the wall plaster
Q 14Which weather keeps nearly all of Winesburg in bed on the night Kate Swift visits George Willard in The Teacher?
Deep snow
Deep snow leaves only four of the town's eighteen hundred citizens awake, and one of them is a minister shivering in a bell tower.
Q 15In the story Hands, Wing Biddlebaum's nervous fingers make him Winesburg's fastest picker of which crop?
Strawberries
Strawberries, as many as a hundred and forty quarts in a day, made his fingers the town's pride, though he spent his life trying to keep them out of sight.
Q 16In Godliness, David Hardy fells his grandfather Jesse Bentley with which weapon before fleeing Winesburg for good?
A sling
A sling he carried for shooting squirrels fires the stone, as Jesse comes running with the long knife meant for a sacrifice; the boy believes he has killed him.
Q 17Helen White, the girl George Willard walks out with in Sophistication, is the daughter of the town's what?
Banker
Banker White owns a new stone house that is one of the prides of Winesburg, and Helen's mother declares nobody in town fit company for her.
Q 18In the prologue to Winesburg, Ohio, an old writer gives which name to people who seize one truth and live by it?
Grotesques
Grotesques are made, in his theory, the moment a person claims a truth as their own, at which point the truth they embraced turns into a falsehood.
Q 19Elizabeth Willard, who once shocked Winesburg by cycling in men's clothes, dreamed as a girl of which career?
Acting
Acting drew her because touring companies lodged with her father, yet the players she confided in told her their life was as dull as the town's.
Q 20Sherwood Anderson modelled fictional Winesburg largely on which real Ohio town, his home from the age of eight?
Clyde
Clyde's streets and townspeople match many in the book, though Anderson claimed the hint for almost every character came from fellow lodgers in a big-city rooming house.
Behind the wall plaster by her bed it stays: she dies before telling George, so the money meant to give him his start in the city lies there undiscovered.
Q 24The long, narrow room at the centre of Loneliness looks out on which public space in New York City?
Washington Square
Washington Square is where Enoch Robinson rents his six-dollar room, shaped like a hallway, and the narrator calls the tale more the room's than the man's.
Q 25In Loneliness, the woman whose visits end Enoch Robinson's happy solitude is thought to play which instrument?
Violin
Violin is only his guess, since he never entered her room; when she walked out for the last time, he says, all his invented company followed her through the door.
Q 26Respectability opens by comparing Wash Williams to which ugly caged animal that city children stop to stare at?
A monkey
A monkey with sagging skin and a purple underbody is the picture, though the narrator admits one part of Wash stays clean and shapely: his hands.
Q 27In Respectability, what does Wash Williams's mother-in-law do that turns his grief into lifelong hatred?
Sends in his wife unclothed
She sends in his wife unclothed, hoping the sight will win him back; he had come ready to forgive, and instead he struck the older woman with a chair.
Q 28Wash Williams tells his tale in Respectability after seeing George Willard kiss which Winesburg hat trimmer?
Belle Carpenter
Belle Carpenter trims hats in Kate McHugh's millinery shop, and Wash says he speaks only to put the young man on his guard against women.
Q 29In The Teacher, what does Kate Swift tell George Willard a writer must learn, instead of fooling with words?
What people are thinking
What people are thinking, not what they say, is her lesson, and she warns him against becoming a mere peddler of words.
Q 30How does Kate Swift suddenly end her embrace with George Willard in the newspaper office in The Teacher?
She beats his face
She beats his face with two sharp little fists and flees, moments before the minister bursts in to proclaim her an instrument of God.