Episode 1
Pooh Bear brings a tricycle to his playdate with Piglet, but Piglet is too afraid to ride again having fallen off once before. To teach Pooh, Piglet must try, try again.
Episode 2
Pooh Bear brings a Jar to his playdate with Piglet. There is just one thing, he doesn't know what's inside!
Episode 3
Pooh Bear is excited to share his harmonica with Tigger, but Tigger is too full of energy to sit still and play. Pooh Bear must play a tune for Tigger to get his bounces out.
Episode 4
Pooh Bear brings a cardboard box to his playdate with Piglet, teaching him that the box can be anything if he uses his imagination.
Episode 5
Kanga teaches Pooh Bear how to play Hide-and-Go-Seek but when Pooh Bear hides he gets the hiccups and is found. Pooh Bear is sad, but then he learns it's his turn to seek now.
Episode 6
Pooh Bear brings a paint set to his playdate with Eeyore. Eeyore finds a butterfly he wants to paint but doesn't have the right colors so Pooh Bear teaches him how to mix colors!
Episode 7
When Pooh Bear brings a kite to his playdate with Piglet, both of them have a hard time flying it. They figure out they can fly the kite by working together!
Episode 8
Pooh Bear and Eeyore go on a treasure hunt. They get stumped on their last clue, but after some encouragement, Eeyore figures it out and they find the treasure!
Episode 9
Pooh Bear teaches Tigger how to keep a hoop from falling to the ground. Pooh Bear tells Tigger that the most important part of trying a new thing is practicing.
Episode 10
Pooh Bear realizes the chalk he brought has turned to dust so Rabbit hops home to get a spare box. Pooh Bear gets bored while waiting for her to return and makes up some games.
Episode 11
Pooh Bear and Piglet make a snow bear together. After they're done, Pooh Bear and Piglet worry that the snow bear will get lonely so, they make a snow pig so that it has a friend.
Episode 12
Pooh Bear brings a bouncy ball to his playdate with Tigger. Tigger suggests a game called 'Big Bounce' and bounces the ball so hard that it almost gets stuck in the tree.
Episode 13
Pooh Bear, Rabbit, and Piglet are having a picnic together. Rabbit brought avocados that she grew in her garden to share, but Piglet is nervous to try a food he hasn't had before.
Episode 14
Pooh Bear and Bea build a pillow fort together at their playdate. But oh no! When they finish building it, they find that it has no doors to go inside.
Episode 15
Kanga brings a blank book to his playdate. Kanga explains that they are gonna fill the book up with their own story. Together Pooh Bear and Bea come up with a story.
Episode 16
Winnie the Pooh brings a music box to his playdate with Tigger and Kanga. They're having a dance party!
Episode 17
Winnie the Pooh and Piglet bring their new sleeping bags to a playdate. They're having a sleepover at the Treehouse!
Episode 18
Winnie the Pooh brings a flying disc to his playdate with Eeyore. When Pooh Bear has to go home to eat and rest, Eeyore feels sad.
Episode 19
Winnie the Pooh brings a pitcher for his playdate with Rabbit. They're going to set up a lemonade stand!
Episode 20
Winnie the Pooh brings a trampoline to his playdate with Tigger so they can bounce around together.
Episode 21
Winnie the Pooh joins Rabbit and Bea for their playdate. Rabbit has grown a pumpkin, and they will turn it into a jack-o'-lantern for Halloween!
Episode 22
Pooh Bear takes Eeyore trick-or-treating for the first time! When they set out and trick-or-treat, Eeyore realizes there is a hole in his bag.
