Winnie the Pooh Trivia
0Loading crowd target
0Loading crowd target
8correct to beat the crowd
104 free Winnie the Pooh trivia questions with answers — literature quiz, new questions added Oct 2026.
Winnie the Pooh is the most famous bear in literary history, and this quiz covers both the bear of the books and the bear of the films. Fifty questions run from A. A. Milne's country home beside Ashdown Forest, the real Canadian bear Winnie at London Zoo and the swan called Pooh, through E. H. Shepard's drawings, Christopher Robin's actual toys (now in the New York Public Library), Eeyore's tail, Piglet's grandfather Trespassers William, Owl's spelling and the game of Poohsticks, to Disney's featurettes, the voices of Sterling Holloway and Jim Cummings, The Tigger Movie and Christopher Robin. Easy questions ask what Pooh loves to eat and who the gloomy donkey is; the hard ones want the year Milne bought the bear at Harrods, which two characters he invented rather than found in the nursery, the price of the original Hundred Acre Wood map at auction and the Latin translation that made the New York Times bestseller list. Written to work for children and adults together, so families can play it as a team. Every answer was checked against Wikipedia's articles on Winnie-the-Pooh and its characters, and each question carries the sentence that backs it up.
30 of 104 questions with answers and explanations. Play the quiz
Q 01Floating up to a bees' nest on a balloon, what does Pooh try to look like?
A small black cloud
A small black cloud: the bees grew suspicious, so Christopher Robin shot the balloon with his gun to bring Pooh gently back down.
Q 02Who illustrated the original Winnie-the-Pooh books?
E. H. Shepard
E. H. Shepard studied Christopher Robin's toys, yet the Pooh he drew looked more like Growler, his own son's teddy bear.
Q 03In Winnie-the-Pooh, Christopher Robin leads an 'Expotition' to find what?
The North Pole
The North Pole: when Roo fell into a stream, Pooh held out a long pole to help him climb out, and Christopher Robin declared it the North Pole.
Q 04What is the name of the forest where the Pooh stories are set?
Hundred Acre Wood
Hundred Acre Wood: the real wood that inspired it is called Five Hundred Acre Wood, and Christopher Robin walked through it on his way to the forest.
Q 05The real forest behind the Winnie-the-Pooh stories is in which English county?
East Sussex
East Sussex: Ashdown Forest lay near the Milnes' country home, and the books' illustrator studied its trees to draw the woods.
Q 06Which London department store did Milne buy his son's teddy bear from in 1921?
Harrods
Harrods: the bear was a present for Christopher Robin's first birthday, on 21 August 1921.
Q 07What was Christopher Robin's teddy bear originally called before it became Winnie?
Edward
Edward: Christopher Robin renamed him after Winnie, a black bear he loved visiting at London Zoo.
Q 08The 'Pooh' part of the name came from what kind of animal?
A swan
A swan: Christopher Robin once called a swan Pooh, and Milne wrote that when they parted they kept the name, thinking the swan wouldn't want it any more.
Q 09Christopher Robin renamed his teddy after a London Zoo bear that had come from which country?
Canada
Canada: soldier Harry Colebourn bought the cub for $20 from the man who had killed her mother and named her after his home town, Winnipeg.
Q 10What was Harry Colebourn, the soldier who bought the bear cub Winnie, by profession?
A veterinary officer
A veterinary officer, Colebourn loaned Winnie to London Zoo when his unit was sent to France, and later donated her to the zoo.
Q 11Where are Christopher Robin's original stuffed toys on display?
The New York Public Library
The New York Public Library: the toys crossed to America with Milne's US publisher in 1947 and were given to the library 40 years later.
Q 12Which two Pooh characters were invented by Milne rather than based on Christopher Robin's toys?
Owl and Rabbit
Owl and Rabbit had no toy models, so the original drawings show them looking more like living animals than stuffed toys.
Q 13Which character was created for the Disney films and never appeared in Milne's books?
Gopher
Gopher was Disney's own addition, reportedly brought in to give the Pooh films a more all-American feel.
Q 21How does Owl spell his own name?
WOL
WOL is how Owl spells his own name, and when Pooh asked him to write a birthday greeting for Eeyore, it came out as 'HIPY PAPY BTHUTHDTH THUTHDA BTHUTHDY'.
Q 22What is the name of Owl's home?
The Chestnuts
The Chestnuts blows down in a storm, and Eeyore finds Owl a new home that turns out to be Piglet's, which Piglet gives up.
Q 23What is the only thing Tigger discovers he likes to eat when he first arrives?
Extract of malt
Extract of malt was Roo's 'strengthening medicine', but Tigger loved it, so he went to live at Kanga's house afterwards.
Q 14What was the title of Milne's 1928 sequel, the second book of stories about the bear?
The House at Pooh Corner
The House at Pooh Corner introduced Tigger and ends with Christopher Robin, growing up, telling Pooh, 'I'm not going to do Nothing any more.'
Q 15Winnie-the-Pooh first appeared by name in a Christmas story in which London newspaper?
Evening News
The Evening News printed 'The Wrong Sort of Bees' on Christmas Eve 1925, and the story became the first chapter of Winnie-the-Pooh.
Q 16What kind of animal is Eeyore?
A donkey
A donkey; Austin, Texas, has held a yearly festival in his honour, Eeyore's Birthday Party, since the 1960s.
Q 17What is Eeyore's favourite food?
Thistles
Thistles: when Pooh sat on one at a picnic, Eeyore asked if he had quite finished with it, then moved over and ate it.
Q 18How does Christopher Robin reattach Eeyore's lost tail?
With a nail
With a nail: Owl had been using the lost tail as a bell-pull, and once Pooh brought it back, Christopher Robin nailed it on again.
Q 19What does Piglet's grandfather's name 'Trespassers William' come from?
A broken sign outside his house
A broken sign outside his house reads 'TRESPASSERS W', and Piglet says his grandfather had two names in case he lost one.
Q 20What kind of tree does Piglet live in?
A beech
A beech: when the rains came, Piglet was trapped in it by the flood and threw out a message in a bottle.
Q 24What is Tigger famous for loving to do?
Bouncing
Bouncing: Eeyore claims he was bounced into the river, and Tigger, who gets the blame, denies it.
Q 25Which friend plots to lose Tigger in the misty forest to make him humbler?
Rabbit
Rabbit's plan backfired: Tigger found his way home, Rabbit, Pooh and Piglet got lost in the mist, and Tigger had to rescue Rabbit.
Q 26Pooh's clock has stopped at what time, meaning it is always nearly snack time?
Five minutes to eleven
Five minutes to eleven: Pooh liked 'a little something' at eleven, and one such snack left him wedged in a friend's front door.
Q 27What birthday present did Pooh give Eeyore?
A useful pot to put things in
A useful pot to put things in: Pooh ate what was inside on the way there, yet Eeyore was delighted with it.
Q 28Which game does Pooh invent on a bridge over the river?
Poohsticks
Poohsticks: the footbridge where Milne and his son played it was later replaced, and the rebuilt original sold at auction in 2021 for over £131,000.
Q 29In which English county is the annual world championship of Pooh's bridge game held?
Oxfordshire
Oxfordshire: the championships began when a Thames lock-keeper saw people playing and turned the game into a fundraiser for lifeboats.
Q 30Which creature do Pooh and Piglet dig a Cunning Trap to catch?
A Heffalump
A Heffalump, an elephant-like beast: the trap caught Pooh instead, with a jar stuck on his head, and Piglet ran off sure he had seen one.