24 Winnie the Pooh Trivia Questions and Answers 

Reading time: 3 Minutes

Do you think you can answer these Winnie the Pooh trivia questions? They aren’t all easy, and I kept hearing Sterling Holloway’s voice in my head when I was writing them. I am that old!

When you read the questions to your kids, use your best Winnie the Pooh voice!

Winnie the Pooh Trivia Questions

  1. Who is the author of the original Winnie the Pooh books?
  2. Who are the inhabitants of the Hundred Acre Wood afraid of, although they have never seen one?
  3. Which character in the Winnie the Pooh universe always loses his tail?
  4. Which character was not in the original A.A. Milne books, but was later added by Disney?
  5. Which character in the Winnie the Pooh universe lives in a tree that says “Mr. Sanders” above his door?
  6. Who illustrated the original Winnie the Pooh books?
  7. Who composed the original music for the Disney adaptations of Winnie the Pooh?
  8. Why is Owl considered one of the wisest residents of Hundred Acre Wood?
  9. Who is the leader of the Hundred Acre Woods in the original books?
  10. What real-life forest inspired the Hundred Acre Wood?
  11. How does Winnie the Pooh spell ‘honey’?
  12. Which character is known for his constant worry and fear?
  13. What does Tigger love to do the most? Answer: Bouncing
  14. What does Winnie the Pooh call a group of bees in the stories?
  15. What is the forest called where the Winnie the Pooh stories take place?
  16. What is the name of the gloomy, pessimistic donkey?
  17. What was Tigger’s first appearance in the books?
  18. What is the reason behind Rabbit’s vegetable garden always being trashed?
  19. What is the name of the book where Winnie the Pooh first appeared?
  20. Who is the smallest character in Winnie the Pooh?
  21. Who is the only female character in the original books? Answer: Kanga In which decade did Disney acquire the rights to Winnie the Pooh?
  22. Where did the name “Winnie” in Winnie the Pooh come from?
  23. What does Eeyore’s name represent phonetically?
  24. What is the full name of the boy who owns Winnie the Pooh?

Winnie the Pooh Trivia Questions and Answers

  1. Who is the author of the original Winnie the Pooh books? Answer: A. A. Milne
  2. Who are the inhabitants of the Hundred Acre Wood afraid of, although they have never seen one? Answer: Heffalumps and Woozles
  3. Which character in the Winnie the Pooh universe always loses his tail? Answer: Eeyore
  4. Which character was not in the original A.A. Milne books, but was later added by Disney? Answer: Gopher
  5. Which character in the Winnie the Pooh universe lives in a tree that says “Mr. Sanders” above his door? Answer: Winnie the Pooh
  6. Who illustrated the original Winnie the Pooh books? Answer: E.H. Shepard
  7. Who composed the original music for the Disney adaptations of Winnie the Pooh? Answer: The Sherman Brothers
  8. Why is Owl considered one of the wisest residents of Hundred Acre Wood? Answer: Because he can read and write
  9. Who is the leader of the Hundred Acre Woods in the original books? Answer: Christopher Robin
  10. What real-life forest inspired the Hundred Acre Wood? Answer: Ashdown Forest in England
  11. How does Winnie the Pooh spell ‘honey’? Answer: ‘Hunny’
  12. Which character is known for his constant worry and fear? Answer: Piglet
  13. What does Tigger love to do the most? Answer: Bouncing
  14. What does Winnie the Pooh call a group of bees in the stories? Answer: A “smackerel” of bees
  15. What is the forest called where the Winnie the Pooh stories take place? Answer: The Hundred Acre Wood
  16. What is the name of the gloomy, pessimistic donkey? Answer: Eeyore
  17. What was Tigger’s first appearance in the books? Answer: “The House at Pooh Corner”
  18. What is the reason behind Rabbit’s vegetable garden always being trashed? Answer: It’s often trashed by the bouncing Tigger
  19. What is the name of the book where Winnie the Pooh first appeared? Answer: “When We Were Very Young”
  20. Who is the smallest character in Winnie the Pooh? Answer: Piglet
  21. Who is the only female character in the original books? Answer: Kanga In which decade did Disney acquire the rights to Winnie the Pooh? Answer: 1960s
  22. Where did the name “Winnie” in Winnie the Pooh come from? Answer: The name “Winnie” comes from a real black bear named Winnipeg that A. A. Milne’s son, Christopher Robin, loved at the London Zoo.
  23. What does Eeyore’s name represent phonetically? Answer: It represents the sound a donkey makes (ee-aw).
  24. What is the full name of the boy who owns Winnie the Pooh? Answer: Christopher Robin Milne

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