Piglet, feeling sorry for Eeyore, who always seems to be depressed, convinces the others to spend a whole day trying to cheer him up.

Piglet sets out with Tigger and Rabbit to the Land of Milk and Honey, hoping to get some honey for Pooh as a gift after Piglet gets an unexpected gift from Pooh. They discover a tiny race of Piglet lookalikes called "Piglies" who elect Piglet their king, which causes him internal conflict--especially when Tigger and Rabbit abuse the Piglies' hospitality.

Tigger encourages Christopher Robin to clean his messy room by throwing everything he owns under the bed. This proves troublesome when the gang discovers that the evil Crud and his sneezing minion, Smudge occupy a land beneath the mattress and plan to spread messiness everywhere.

All the honey in the Hundred-Acre Wood has disappeared and it appears to be the work of a Heffalump and a Woozle named Heff and Stan. When the gang successfully recovers the honey, Stan decides to get backup in the form of a giant Woozle named Wooster--but Pooh's offer of friendship provides a surprising resolution to the conflict.

Christopher Robin and the gang get into mischief while a babysitter tries to look after them.

After being buffeted about by the wind, Piglet becomes afraid of going outside.

Pooh and Piglet help a young heffalump who is having difficulty learning trapping from his father.

The gang is in a state of panic because they think they are being haunted by a ghost which was just Piglet running scared silly.

When Christopher Robin shows Pooh a wishing star, Pooh tells Piglet, Tigger and Rabbit about it, and they all wish for something. But, when Pooh thinks he wished out the wishing star, and that the others' wishes will not come true, he tries his best to fulfill them all.

Pooh and the gang try to deal with the pack rats during a flood.

Piglet saves Tigger's life, and Tigger becomes Piglet's servant.

Rabbit builds a fortress to prevent anyone from trampling into his garden only to realize that he has forgotten to put a door, thus trapping himself inside.

Eeyore becomes sick of his tail, so he abandons it. But Eeyore decides he wants it back, and Detective Tigger helps him. But the others find it and claim it as an object of their own.

Owl wants to see his family, so Pooh and Piglet organise a family reunion for him. But does Rabbit think they're true?

Tigger befriends a termite which had been eating all the wooden things in the Hundred Acre Wood. And Rabbit tells Tigger to get rid of the termite.