The story opens with a bear named Winnie-the-Pooh in the Hundred Acre Wood going through his morning stoutness exercises, during which he accidentally rips the stitching on his bottom. After repairing his torn rump, he discovers that his jar of honey is nearly empty and starts wondering where he can get honey as he eats what's left in the pot. He hears a bee fly by, and tries pulls his head out of the jar, then decides to try to get honey from the bee's hive in the nearby honey tree.

He first tries climbing the tree, but that doesn't work when the branch he's standing on breaks, and he tumbles to the ground into a "gorse-bush". He then borrows a blue balloon from a boy named Christopher Robin in an attempt to fool the bees and get the honey. Cleverly, Pooh disguises himself as a little black rain cloud by dunking himself with mud, and then uses the balloon to float up next to the hive. A lone bee guard flies out to meet him and is very wary of the little black rain cloud. Pooh Bear sticks his hand into the hive and pulls out a giant handful of honey with bees on it eats the honey and spits the bees out. Among them is the queen bee, who is kicked by Pooh Bear and falls into the same muddy spot in which he disguised himself.

Pooh is soon surrounded by angry bees from the hive, his disguise wearing off. After getting out of the mud puddle, the queen bee sees the little black rain cloud is a bear. Angry, the bee shoots up toward Pooh and stings his bum. The sudden hit causes Pooh to swing upward and back, jamming his rear into the bottom of the hive. The head bee rests on a nearby branch and starts laughing heartily at Pooh Bear's expense. The now nervous Pooh Bear admits to Christopher Robin that these are the wrong sorts of bees, and is shoved out of the hole by the incensed insects who proceed to give chase.

During the pursuit, the string holding the balloon closed comes loose and the balloon flies out of control. Pooh Bear is taken for a wild ride. The queen bee continues laughing but is now forced to take cover as her quarry whizzes by her twice. The chase is suddenly reversed as the bees are now chased by Pooh Bear. The bees retreat into their hive and Pooh Bear's balloon deflates its last bit of air. The defeated bear inevitably falls back to earth and lands in the arms of Christopher Robin. The queen bee calls the others to attention with a buzzing "CHARGE!" and the swarm gives chase after the two who seek safety in the mud puddle. Pooh then confesses, "You never can tell with bees!" before spitting out one more bee. Pooh Bear visits Rabbit, hoping to finding honey there. Although Rabbit is aware of the bear's vast appetite, he welcomes him for lunch and gives him a small drop of honey. The honey, however, doesn't fill Pooh's stomach all the way. So he asks for more. Rabbit is hesitant but agrees, and so in a very gluttonous manner, Pooh devours ten jars of honey. Pooh Bear, his face covered with honey, thanks Rabbit and eats leftover honey on his stomach, which is now extremely round and full. He tries to leave through Rabbit's front door, but has become extremely large from the vast amount of honey he has eaten — so fat that Pooh gets stuck in Rabbit's front door. Rabbit tries to free Pooh by pushing his over-sized bottom but it isn't any use. He goes round to the front of the house to face Pooh's head, and tells Pooh, truthfully, that he has eaten too much, and as a result, he has grown too fat for rabbit's front door (Rabbit says it has happened because Pooh has eaten too much but Pooh claims it has happened because Rabbit's front door isn't big enough). Rabbit then goes off to find Christopher Robin for help. While he waits, Pooh Bear is visited by Owl and Gopher. Owl analyzes Pooh's peculiar situation and decides that the intervention of an expert is necessary. Gopher offers to free Pooh Bear using dynamite, but Owl angrily declines. Gopher turns to leave and falls into one of his holes Christopher Robin, Rabbit, and Eeyore arrive and try to help Pooh Bear but they can't budge him one inch from all the honey. Christopher Robin suggests pushing him back in but Rabbit protests. So everyone comes to a solution; Pooh will abstain from eating until he slims down. Rabbit is forced to make the best of a bad situation, and devises various ways to disguise the bear's bottom, which turns out not to be a good idea (Pooh sneezes from honeysuckle just as Rabbit is decorating his behind as an antiques shelf). One night, as Pooh sleeps, Gopher suddenly reappears, preparing to have his midnight snack when Pooh suggests that Gopher allow him to 'just taste' some of his honey. Gopher agrees to allow this, but soon Rabbit, fearing an extended period of Pooh being stuck, runs outside and posts a sign forbidding anyone to feed Pooh at all (Rabbit: "Don't Feed The Bear!"). Miffed by this ruling, Gopher decides to leave and falls into his hole again. As the days go by, Pooh Bear finally slims down enough to be freed. Christopher Robin, Kanga, Eeyore, Owl, Roo, and Gopher (who falls into his hole once again when Eeyore's tail is accidentally pulled off by both him and Roo) start pulling on Pooh Bear while Rabbit pushes from behind but the bear won't move Fed up with all this delay, Rabbit takes several steps backwards and charges into Pooh Bear. Rabbit's push catipults Pooh into the air, sending the other's sprawling to the ground, towards the forest. (In a sight gag, Pooh almost flies out of the book, but is pushed back by the turn of a page at Gopher's harried insistence.) Pooh Bear comes in for a landing in the hole of a similar honey tree, flushing out a swirling swarm of bees. The gang runs after him and finds him stuck in the honey tree. Christopher Robin tells Pooh that they will help him get out again but Pooh tells them to take their time; the bees were scared away by his abrupt arrival giving the silly old bear a chance to enjoy a hive full of his favorite honey. At the next chapter Pooh visits his thoughtful spot to think. Gopher tells Winnie the Pooh that it is "Winds-day" (a play on "Wednesday"), whereupon Pooh decides to wish everybody "Happy Winds-day." He visits his friend, a little pig named Piglet, who wears a scarf around his neck on this day. Piglet is blown into the air, his scarf unraveling all the while, and Pooh grabs hold of him. As they fly like a kite through the air over the other characters' heads, Pooh wishes Kanga, Roo, Eeyore, Rabbit, and Owl a happy Winds-day. However, once they arrive at Owl’s treehouse, he informs them that the wind is due to "a gentle spring zephyr" rather than to a particular holiday. During the windstorm, Owl's house is knocked down, so Eeyore volunteers to house-hunt for Owl That night, Pooh hears an unfamiliar noise coming from elsewhere in the Hundred Acre Wood. Someone knocks on Pooh’s door, then a bouncy tiger named Tigger bounces inside in search of something to eat. After That he tries some honey but decides, "Yuck! Tiggers don't like honey." Before leaving Pooh’s house, Tigger tells him that there are Heffalumps and Woozles in the forest that steal honey, Pooh's favorite food. Later, Pooh suffers from a nightmare in which Heffalumps and Woozles steal his honey Later that night, a storm floods the Hundred Acre Wood. Piglet, who is trapped in his home, writes a bottle-note for help just before the waters carry him away riding a chair. Pooh, who is trapped in a honey pot, floats away from his home as well. The remaining characters gather at Christopher Robin's house, and Christopher reads the message ("Help! P-P-P-Piglet [Me]!"). He then sends Owl to inform Piglet of a rescue plan in the works, but just after he delivers the news, Piglet and Pooh are mixed up in a waterfall which switches Piglet to the honey pot and Pooh to the chair. When they arrive together at Christopher Robin’s house, he mistakenly thinks that Pooh rescued Piglet, and throws a hero party for Pooh. During the party, Eeyore announces that he has found a new home for Owl. But everyone unfortunately learns that the one Eeyore found is Piglet's house, they become shocked and try to tell Eeyore that Piglet already lives there. However, Piglet decides to reluctantly give his home to Owl, and Pooh offers to let Piglet live with him. Pooh suggests to Christopher Robin that the hero party should become a two-hero party because of Piglet’s generosity. He agrees, and the characters celebrate both Pooh’s and Piglet's good deeds that day. In the final part of the story, Tigger has been bouncing on anyone he comes across for fun, which gets on Rabbit's nerves. After holding a meeting with Pooh and Piglet, Rabbit decides to take everyone, including Tigger, out into the Hundred Acre Wood. But during the trip, Rabbit, Pooh, and Piglet purposefully ditch Tigger on the hopes he would get lost. The three hide in a log as Tigger searches for them. The three try to make it back home, but end up at a certain spot. Pooh offers a silly suggestion to search for that same spot, and Rabbit abandons them to try to prove Pooh wrong. Pooh and Piglet find their way out of the forest by themselves where they come across Tigger. Tigger reveals that Tiggers don't get lost easily. Tigger finds out that Rabbit is still in the forest so he goes off to find him. Rabbit is lost and as he's finding his way home, and ends up in a dark, damp & misty part of the forest, too add to that he's scared by various animal noises such as crickets, caterpillars, frogs, snakes and woodpeckers. Frogs start croaking loudly, caterpillars munch loudly on leaves and after seeing frogs sitting there in front of him (plus more appearing and making more noise) it scares the living daylights out of him. The sounds get to him so badly that it drives him mad causing his eyes to make whirlpools and he frantically tries to run away only to be tackled by Tigger. Tigger then takes Rabbit home It's now snowing and Roo wants to go play. Kanga can't be with him, so she calls on Tigger to look after Roo which he gladly accepts. Along the way through the woods, Tigger and Roo see Rabbit skating on the ice. Tigger tries to teach Roo how to ice skate by doing it himself, but unfortunately, he loses his balance and collides with Rabbit and the result is Tigger sliding across the ice into a snowbank and Rabbit crashing into his house. Tigger then decides that he doesn't like ice skating. Later on, while bouncing around the woods with Roo on his back, Tigger accidentally jumps too high up a tree and is too scared to get down. He calls for help and Pooh and Piglet come to the scene. Roo successfully jumps down but Tigger refuses to follow suit Soon, Christopher Robin, Rabbit and Kanga arrive and try to convince Tigger to jump. Eventually, Rabbit decides that the group would just have to leave Tigger in the tree forever, on which Tigger promises never to bounce again if he ever was released from his predicament. Christopher Plummer the narrator) chimes in for help. Tigger begs Plummer to "narrate" him down from the tree, and Plummer tilts the book, allowing Tigger to step onto the text of the page. Tigger starts to feel better that he make it this far and before he can do otherwise, Plummer tilts the book again causing Tigger to fall down into the snow. Happy, Tigger attempts to bounce but Rabbit stops him reminding Tigger of the promise he made. Devastated, Tigger slowly walks away and Rabbit feels better that there will be peace. But everyone else is sad to see Tigger like this and remind Rabbit of the joy Tigger brought when he was bouncing. Suddenly, Rabbit feels sorry for Tigger and takes back the promise he made and is given a friendly tackle by an overly-excited Tigger. Tigger invites everyone to bounce with him and even teaches Rabbit how to do it. For the first time, Rabbit is happy to be bouncing, with everyone else and Tigger sings his trademark song for the last time. For the finally, after a lecture done by Christopher Robin and Pooh and when the book closes, a live action Pooh Bear (through stop motion animation) winks at us, ending the story.