Winnie the Pooh Day Activities

Winnie the Pooh Day Activities

Are you looking for Winnie-the-Pooh Day activities? Winnie-the-Pooh Day is celebrated on January 18th every year, which is the birthday of the author A.A. Milne. This day provides a fantastic opportunity for upper elementary teachers to engage their students in fun and educational activities centered around the delightful world of Winnie-the-Pooh.

The beloved character has been enchanting readers for almost a century and originated in the creative mind of A.A. Milne. Milne bought a stuffed toy for his son Christopher Robin at Harrods Department Store and began making up adventures featuring the toy for his son.

The world learned of Winnie-the-Pooh after London’s Evening News commissioned Milne to write a story for Christmas Eve 1925. Teachers can continue sharing Winnie-the-Pooh’s magic with their students today. This post includes activities ranging from reading comprehension and writing to hands-on fun.

Be sure to get the handout. It includes the printables you need to complete some of the activities.

Winnie-the-Pooh Day Activities

Activity #1: Read a chapter from the original book.

Winnie the Pooh Day Activities for Big Kids

One of the best ways to celebrate Winnie-the-Pooh Day is to read a chapter from the original book by A.A. Milne, which is now in the public domain. You can find the full text online here

In the handout, I have included “Chapter II: In Which Pooh Goes Visiting and Gets Into a Tight Place,” which tells how Pooh got stuck in Rabbit’s Hole after overeating honey. Afterward, students can answer comprehension questions to assess their understanding of the text. 

Depending on their level and preference, you can have your students answer these questions orally or in writing.

Activity #2: Winnie-the-Pooh Videos

Another fun Winnie-the-Pooh Day activity is watching videos related to Winnie-the-Pooh and his friends. You can find many videos online that are suitable for upper elementary students, such as:

Activity #3: Character Trait Matching Cards

Character Trait Cards

In this activity, students will use Character Trait Matching Cards to analyze the personalities of the main characters in the book. The cards include the following:

  • an illustration and character name
  • personality traits
  • evidence from the text for one or more of the personality traits

Students will work in groups of 2-3 to match the cards for each character and discuss their matches with their group members. As an extension activity, students can create their Character Trait Matching Cards for other characters or characters in other books.

Matching games that students can play with these cards include Memory Match, Go Fish, and Charades.

Activity #4: Map of the Hundred-Acre Wood

Provide students with quotes from the book that describe the Hundred Acre Wood. Ask them to use their imagination to draw a map with key locations from the stories, such as Pooh’s house, Piglet’s house, Rabbit’s house, and the spot where Eeyore’s Gloomy Place is situated. This activity will help students visualize the world of Winnie-the-Pooh and develop their map-reading skills.

After students finish their maps, show them the map from the novel, which I have included in the “Student Packet” for comparison.

Activity #5: Kenny Logans and “House at Pooh Corner”

House at Pooh Corner

Kenny Loggins and his song “House at Pooh Corner” is a great activity to engage students on Winnie-the-Pooh Day. This article provides insights into the inspiration and creation of the iconic song by Kenny Loggins. It explores Loggins’ connection to the story of Winnie-the-Pooh and how it resonated with his own experiences and emotions during a significant time in his life.

By reading this article, students can gain a deeper understanding of the song’s meaning, its connection to the beloved characters from The Hundred Acre Wood, and the creative process behind its composition. They can explore nostalgia, loss of innocence, and the enduring appeal of childhood stories.

Along with the article, teachers can provide a set of comprehension questions that encourage students to reflect on the song’s deeper emotions conveyed through the lyrics.

Activity #6: Pooh’s Creative Corner 

Set up a creative corner in the classroom with art supplies and materials for students to create their Winnie-the-Pooh-inspired artwork. Please encourage them to draw scenes from the stories, illustrate their favorite quotes, or even design their book covers for a Winnie-the-Pooh sequel.

Activity #7: Winnie-the-Pooh Snack Mix

Winnie the Pooh Day Activities for Big Kids


Mix equal parts of each of the following ingredients:

  • Honeycomb cereal (to represent Pooh’s love for honey)
  • Teddy Grahams (to represent Winnie-the-Pooh)
  • animal crackers (to represent the animals in the Hundred Acre Wood)
  • pretzels (to represent sticks)
  • popcorn (to represent Piglet’s love for popcorn)
  • dried cranberries (to represent berries found in the Hundred Acre Wood)
  • mini marshmallows (to represent the water)

Mix all the ingredients gently, ensuring an even distribution of each component. You can divide the snack mix into portions or small bags for easy student distribution.

This Winnie-the-Pooh Snack Mix brings the story to life while providing a delicious, classroom-friendly snack. It allows students to engage with the symbols and elements of the story in a fun and tasty way, making Winnie-the-Pooh Day even more memorable. Enjoy!

Winnie-the-Pooh Day provides an excellent opportunity to celebrate the timeless charm of this beloved bear and engage students in meaningful and enjoyable activities. By incorporating reading, comprehension, writing, art, and even animated videos, teachers can create an educational experience that brings the world of Winnie-the-Pooh to life in the classroom.

These activities foster a love for literature and promote critical thinking, creativity, and social-emotional development in upper elementary students. So, let’s embark on an adventure in the Hundred Acre Wood and celebrate the magic of Winnie-the-Pooh together!

Gay Miller

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