Sideways Stories from Wayside School
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40 free Sideways Stories From Wayside School trivia questions with answers — literature quiz, new questions added Oct 2026.
Louis Sachar's Sideways Stories from Wayside School has been making children laugh since the 1970s. The school was built by mistake as a tower with one classroom on every floor, and each short chapter follows a different pupil or teacher through a day where the ordinary rules do not quite apply. This quiz works through the book chapter by chapter: Mrs. Gorf and her terrible punishment, Mrs. Jewls and her odd ideas about teaching, the pupils and their peculiar problems, and Louis, who watches over the playground. A few questions look at how the book came to be written and what became of it afterwards. It suits readers who have just finished the book, classes reading it together, and adults who remember it fondly. Every answer comes with a short explanation, so a wrong guess still teaches something.
30 of 40 questions with answers and explanations. Play the quiz
Q 01At Wayside School, Mrs. Gorf wiggles her ears and sticks out her tongue to turn students into what?
Apples
Apples piled up on Mrs. Gorf's desk, so a visitor assumed the children adored her. She ended up as one herself and was eaten.
Q 02At Wayside School, which object does Jenny hold up so that Mrs. Gorf's spell lands on the teacher herself?
A mirror
A mirror turned Mrs. Gorf's own magic back on her, and Louis, not knowing what had happened, polished her on his shirt and ate her.
Q 03Which story of Wayside School was never built, so that its teacher and her class do not exist either?
The nineteenth
The nineteenth story is missing, so the book's chapter with that number is missing too, with an apology printed in its place.
Q 04At Wayside School, new teacher Mrs. Jewls thinks her pupils are so cute they must be which animals?
Monkeys
Monkeys were her first guess, because she had never seen children so cute. The class rather preferred being treated that way.
Q 05At Wayside School, what is the rude new pupil Sammy revealed to be beneath his many smelly raincoats?
A dead rat
A dead rat was all that remained once the coats came off, and Mrs. Jewls threw it away. It was the third to try sneaking into her class since September.
Q 06Three boys in Mrs. Jewls's class at Wayside School share which first name and get unfair nicknames for it?
Eric
Eric is the name of three classmates, surnamed Bacon, Fry and Ovens, and each is teased for a fault that only the other two have.
Q 07At Wayside School, which treat does Maurecia eat for lunch every day until she has tried every flavor?
Ice cream
Ice cream bores Maurecia once no new flavors are left, so Mrs. Jewls invents one named after each pupil in the class.
Q 08At Wayside School, what does Paul keep tugging until Leslie yells and his name goes on the board?
Her pigtails
Her pigtails tempt Paul so much that he imagines one of them talking to him, and he is sent home after her third yell.
Q 09At Wayside School, round-headed John has a reading problem: he can only read words turned which way?
Upside down
Upside down was the only way John could read until a fall while standing on his head flipped his brain the right way.
Q 10Which Newbery Medal winner, later a Disney film, is by the author of Sideways Stories from Wayside School?
Holes
Holes won the 1999 Newbery Medal, and Louis Sachar wrote the screenplay for the film himself, even appearing briefly on screen.
Q 11At Wayside School, Rondi loses her temper with Louis after he compliments which things she does not have?
Her front teeth
Her front teeth are missing, and people keep admiring the gap, which baffles Rondi until one compliment too many makes her snap.
Q 12At Wayside School, Stephen alone dresses up for a class party held on the Friday before which holiday?
Halloween
Halloween fell on a Sunday that year, so Stephen reasoned it should be marked on the Friday. Mrs. Gorf's ghost turned up, agreed with him, and vanished when he hugged her.
Q 13What is the job of Louis at Wayside School, a role author Louis Sachar once held at a real school?
Yard teacher
Q 21Which pupil at Wayside School sleeps through lessons in a huge coat and once tumbles out of the window?
Sharie
Sharie is left to doze because Mrs. Jewls believes children learn best asleep, and Louis saves her at the last moment.
Q 22At Wayside School, Mrs. Jewls tells Bebe Gunn that quality matters more than speed in which activity?
Drawing
Drawing is Bebe's gift: she turns out hundreds of pictures in an hour, then goes home to start one cat she expects to have barely begun by morning.
Q 23At Wayside School, Mrs. Jewls stops which of Dana's itchy troubles by turning them into arithmetic problems?
Mosquito bites
Mosquito bites covered Dana so badly she could not concentrate, until treating them as numbers in sums made the itching stop.
Yard teacher was what pupils called Louis Sachar when he supervised their lunchtime play, and the final chapter reveals his namesake wrote the book.
Q 14Mrs. Jewls's classroom sits on which story of Wayside School, the highest in the building?
The thirtieth
The thirtieth story tops a school built with one classroom per floor, after the builder stacked rooms that were meant to sit in a row.
Q 15At Wayside School, a pupil whose name Mrs. Jewls circles on the board is sent home early on what?
The kindergarten bus
The kindergarten bus leaves at noon, and one well-behaved boy ends up riding it home every single day on a third strike.
Q 16At Wayside School, Jenny arrives late to find an empty classroom and strange men because it is which day?
Saturday
Saturday was why nobody else had come, and the men with an attaché case questioned Jenny before warning her not to do it again.
Q 17At Wayside School, Myron is given which job, whose only duty is turning the classroom lights on and off?
Class president
Class president sounded grander than flicking a switch, and Myron lost the title after one day, arriving late the morning after he saved a dog.
Q 18At Wayside School, Louis refuses to watch a class film about which animals because they are too slow?
Turtles
Turtles were the subject of the film, and Dameon missed all of it running up and down the stairs to answer Louis's questions about it.
Q 19Which well-behaved boy in Mrs. Jewls's class at Wayside School is punished daily and once outwits robbers?
Todd
Todd hands the robbers a classmate's workbook instead of money, gets a standing ovation, and is still sent home early.
Q 20Which curly-haired boy at Wayside School counts in the wrong order yet always lands on the right answer?
Joe
Joe wakes up one morning suddenly able to count properly, and celebrates by counting every hair on his head.
Q 24At Wayside School, Jason is stuck to his chair by chewing gum until what finally frees him?
A kiss on the nose
A kiss on the nose from the girl who put the gum there makes Jason fall off his seat, and it saves her from being sent home.
Q 25At Wayside School, what does Leslie try to sell Louis for five cents each because she finds them useless?
Her toes
Her toes stay unsold: Louis haggles the price down for the small ones, and Leslie refuses to break up the set.
Q 26At Wayside School, small-footed Ron wants to join which playground game that nobody will play with him?
Kickball
Kickball finally happens when Louis teams up with Ron against the whole class. When Louis scolds his weak kicking, Ron's punch proves far harder than his kick.
Q 27At Wayside School, a shy boy embarrassed by his girlish name swaps it for Mac; what was he called before?
Nancy
Nancy went to a girl from another class who had hated being Mac, and soon the whole class was trading names in confusion.
Q 28Which teacher at Wayside School is said to teach on the story that was never built, so she is not there?
Miss Zarves
Miss Zarves gets a chapter that is not there either, and one boy is thanked for delivering her a note that was never written.
Q 29Louis of Wayside School, a character based on the author, has which feature in many colors?
A mustache
A mustache of many colors marks out Louis, who is friends with every child at the school and turns out to be the storyteller.
Q 30Robbers burst into Mrs. Jewls's classroom at Wayside School because they mistook the building for what?
A bank
A bank was what they expected, and they leave with nothing but a pupil's workbook, handed over by a quick-thinking boy.