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60 free Winnie the Pooh trivia questions with answers — literature quiz, new questions added Aug 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 60 questions with answers and explanations. Play the quiz
Q 01Who wrote the Winnie-the-Pooh books?
A. A. Milne
Milne was a Londoner and Punch contributor who bought a country home near Ashdown Forest in 1925.
Q 02Who illustrated the original Winnie-the-Pooh books?
E. H. Shepard
Shepard based his drawings of Pooh not on Christopher Robin's bear but on his own son's teddy, Growler.
Q 03What is Pooh's favourite food?
Honey
He spells it 'hunny' and likes 'a little something' at around eleven in the morning.
Q 04What is the name of the forest where the Pooh stories are set?
Hundred Acre Wood
It was based on the real Five Hundred Acre Wood in Ashdown Forest, East Sussex.
Q 05The real forest that inspired the stories is in which English county?
East Sussex
Milne's country home was Cotchford Farm near Hartfield, a mile north of Ashdown Forest.
Q 06Which London department store did Milne buy his son's teddy bear from in 1921?
Harrods
The boy first called it Edward, then renamed it after a bear at London Zoo.
Q 07What was Christopher Robin's teddy bear originally called before it became Winnie?
Edward
The bear made his debut as Edward in Milne's 1924 poem 'Teddy Bear' in Punch.
Q 08The 'Pooh' part of the name came from what kind of animal?
A swan
Pooh the swan even appears as a character in his own right in When We Were Very Young.
Q 09The real bear Winnie at London Zoo was named after which city?
Winnipeg
Lieutenant Harry Colebourn bought the cub for C$20 in White River, Ontario, on his way to the First World War.
Q 10What was Harry Colebourn, the soldier who bought the bear cub Winnie, by profession?
A veterinary officer
He left Winnie at London Zoo while serving in France and donated her officially after the war.
Q 11Where have Christopher Robin's original stuffed toys been displayed since 1987?
The New York Public Library
They went to the US with Milne's American publisher in 1947 and were donated to the library in 1987.
Q 12Which two Pooh characters were invented by Milne rather than based on Christopher Robin's toys?
Owl and Rabbit
Piglet, Eeyore, Kanga, Roo and Tigger were all real nursery toys.
Q 13Which character was created for the Disney films and never appeared in Milne's books?
Gopher
Disney licensed the film rights from Milne's widow and the Slesinger estate in 1961.
Q 21What kind of tree does Piglet live in?
A beech
Piglet's favourite food is acorns, which the book spells 'haycorns'.
Q 22How does Owl spell his own name?
WOL
He also wrote 'HIPY PAPY BTHUTHDTH THUTHDA BTHUTHDY' on Eeyore's birthday pot.
Q 23What is the name of Owl's home?
The Chestnuts
It is described as an 'old world residence of great charm', until it blows down in a storm.
Q 24What is the only thing Tigger discovers he likes to eat when he first arrives?
Q 14In which year was the book Winnie-the-Pooh first published?
1926
The first story had already appeared in London's Evening News on Christmas Eve 1925.
Q 15What was the title of Milne's 1928 sequel, the second book of stories about the bear?
The House at Pooh Corner
It introduced Tigger, the only major new character in the second book.
Q 16Winnie-the-Pooh first appeared by name in a Christmas story in which London newspaper?
Evening News
The Christmas Eve 1925 story became the first chapter of the book.
Q 17What kind of animal is Eeyore?
A donkey
His name mimics a bray, 'hee-haw', as heard in a non-rhotic English accent.
Q 18What is Eeyore's favourite food?
Thistles
His home is marked on the map as 'Eeyore's Gloomy Place: Rather Boggy and Sad'.
Q 19How does Christopher Robin reattach Eeyore's lost tail?
With a drawing pin
Owl had mistaken the tail, with its pink bow, for a bell-pull.
Q 20What does Piglet's grandfather's name 'Trespassers William' come from?
A broken sign outside his house
The sign reads 'TRESPASSERS W', which Piglet explains is short for Trespassers Will, short for Trespassers William.
Extract of malt
Kanga keeps it on hand as 'strengthening medicine' for Roo.
Q 25What does Tigger say Tiggers do best?
Bouncing
He arrives at Pooh's door in the middle of the night, announcing himself with a stylised roar.
Q 26Who hatches the plan to 'unbounce' Tigger by getting him lost in the mist?
Rabbit
The plan backfires and Pooh finds the way home by following the 'call' of his honeypots.
Q 27Pooh's clock has stopped at what time, meaning it is always nearly snack time?
Five minutes to eleven
Pooh makes a habit of having 'a little something' around eleven in the morning.
Q 28What did Pooh end up giving Eeyore for his birthday after eating the honey on the way?
A useful pot to put things in
Piglet's balloon burst on the way too, but it fitted neatly inside the empty pot.
Q 29What game do Pooh and his friends play by dropping sticks off a bridge?
Poohsticks
Milne and Christopher Robin really played it on a footbridge near Cotchford Farm, which is now a tourist attraction.
Q 30In which English county is the annual world championship of Pooh's stick-dropping bridge game held?
Oxfordshire
The game began in The House at Pooh Corner before crossing into real life.