Pooh (Sterling Holloway), a bear of very little brain, lives with all his friends in the Hundred Acre Wood. Pooh’s friends include the gloomy donkey Eeyore (Ralph Wright), Kanga (Barbara Luddy) & Roo (Clint Howard and Dori Whitaker), Tigger (Paul Winchell), Piglet (John Fiedler), Rabbit (Junius Matthews) and Owl (Hal Smith).

Pooh lived in a small house, with the name plate of Mr Sanders.

Winnie is hungry after his morning exercise, but he finds that he is out of honey. Pooh decides to get honey from a bee-hive in a tree. He climbs a tree but slips (when a branch breaks under his weight) & falls all the way down. Pooh thinks again about how to get some honey.

Next, Pooh visits his friend Christopher Robbins (Bruce Reitherman, Jon Walmsley and Timothy Turner), who was pinning a tail on Eeyore the donkey to cheer him up. Christopher lived in another part of the Hundred Acre Wood.

Pooh borrows a balloon & rolls himself in mud until he is covered in mud from head to toe. Pooh then grabs hold of the balloon and rises to the bee-hive. By that time, some of the mud comes off and Pooh is identifiable again.

As he approaches the bee-hive, the bees see through his plan & attack him. The balloon comes undone and Pooh falls to the ground and the bees follow him. Pooh & Christopher have to hide inside the mud pool under their umbrella to save themselves.

Pooh is still hungry and is not about to give up easily. Pooh decides to visit Rabbit for lunch. Rabbit tries to avoid him, but Pooh comes inside uninvited & finishes all of Rabbit’s honey. Rabbit’s house is accessible only through a narrow hole which serves as both the entry and exit. Pooh gets stuck in the Rabbit hole trying to get out. The Owl gets a gopher (Howard Morris) to dig Pooh out, while Rabbit summons Christopher. The gopher says that it would take 3 days to dig Pooh out of the hole he is stuck in. Gopher suggests using dynamite to speed up the process and Owl cannot seem to negotiate a rate for his services.

They all fail & the only option is to wait till Pooh gets thin again. Meanwhile, Rabbit decides to decorate the area around Pooh’s behind as he is stuck looking at it for several days. But every time Pooh sneezes, it messes up everything inside Rabbit’s home and he gives up. Due to Pooh’s snoring at night, Rabbit is unable to get any sleep at all. Rabbit prohibits everyone from feeding Pooh, despite Pooh’s protests.

Days pass & Rabbit has given all hope, when 1 day he budges. The whole gang pitches in to pull Pooh & when he does come out, he projectiles & strikes the bee tree. All the bees’ escapes, leaving Pooh with all the honey.

Winter arrives & its windy. Pooh was out for a stroll and Piglet was cleaning his front yard. Piglet is too light, and it swept away and carried by the wind. He runs into Pooh who tries to grab Piglet’s scarf, which turns Piglet into a kite. Piglet & Pooh get carried away to Owl’s house in the trees. On the way, Pooh runs into Eeyore’s home and ends up destroying it. They then slide through Rabbit’s Garden and end up harvesting all his carrots, which helps Rabbit to save the effort of doing it himself.

The wind is so strong that it brings the tree down & Owl’s house is destroyed along with it. Donkey promises to find Owl a new house.

That night it starts to rain heavily & Tigger makes his entrance in Pooh’s house. Tigger says that he also likes Honey and proceeds to eat some from Pooh’s jars. He tells Pooh that elephants & weasels like honey & steal it from bears. Tigger then leaves, but Pooh is now worried for his honey and decides to guard it. He soon falls asleep and has nightmares of elephants and weasels stealing his honey. Pooh wakes up with a startle to find his house being flooded with rainwater.

As the rain increased, it started flooding the Hundred Acre Wood, starting with Piglet’s house. All of them gather at Christopher’s house as it is still above water. Roo discovers a bottle message from Piglet asking for help. Christopher dispatches Owl to fly to Piglet’s house and to rescue him.

While Owl rescues Piglet, they both go over a waterfall, with Piglet taking shelter inside a honey pot. Pooh also goes over the same waterfall and is found by Christopher. Christopher declares that Pooh is a hero for saving Piglet and throws a feast in his honor.

As waters recede Donkey declares that he has found a new house for Owl. But he takes them to Piglet’s house. Piglet doesn’t say that it is his house as he knows Owl is in need. So, Pooh offers Piglet that he should stay with Pooh.

The bouncing Tigger destroys Rabbit’s cabbage patch. Rabbit holds a protest meeting with Pooh & Piglet to get Tigger to stop bouncing. His plan is to lose Tigger in the forest for a day. The 4 set off into the forest & they lose Tigger. But they get lost themselves & its Tigger who finds them & takes them home.

Then One day Tigger bounces up a tree & gets stuck as he is afraid to come down. The whole gang assembles & Tigger promises that if he gets out of this trouble, he will never bounce again. Rabbit holds Tigger to his promise once he is eventually down. This makes Tigger sad as he can’t bounce ever again. The gang is sad for Tigger as they really liked the bouncy Tigger best. So, Rabbit takes back the promise & allows Tigger to bounce again. Tigger is happy & he reminds Rabbit that he can bounce too. Rabbit tries that & realizes that he likes bouncing too.