As a reward for Christopher Robin eating all his vegetables, he along with Pooh, Piglet, and Tigger go to the theater to watch Birdzilla, a scary monster movie. During the film, Piglet gets scared and thinks the movie is real and the monster will get him. The gang tries to convince him that it's only make-believe and proceed to make their own monster film to prove it.
Eeyore is sitting on top of the hill outside of Piglet's house. Piglet is saddened that Eeyore is so gloomy, so he decides to do something about it. He, along with Pooh, Rabbit, Tigger, Owl, Eeyore, and Roo, each try to cheer him up by trying various things.
Pooh has been borrowing too much honey from Rabbit lately. This makes Rabbit mad to the point where he says that Pooh is "eating him out of house and honey". Desperate, Pooh and his friends try to retrieve honey from a beehive, so Rabbit won't have to move away. Nevertheless, this proves to be a daunting task.
Pooh and Tigger invite Piglet to join them for a camping trip. This comes at a very bad time for Piglet as he just awoke from a nightmare about Heffalumps and Woozles. After some convincing and pushing in the direction of the site, Piglet agrees to join them. However, things become complicated as they soon come face-to-face with some mysterious creatures.
Pooh decides to pay his best friend, Christopher Robin a visit. Christopher surprises Pooh with a balloon. Intrigued, Pooh asks to borrow it. He agrees to the condition that Pooh take care of it "as if it were a pot of honey". When Rabbit sees the balloon, he has other plans in mind.
During a winter snowstorm, Rabbit and his friends are trying to save a late blooming carrot. In the midst of this, they hear a baby bluebird named Kessie who is being blown away by the wind. Rabbit rescues it and decides to take care of it. Things go well until next winter when Kessie, now older, needs to migrate south.
Pooh is looking through his closet and happens upon a spring from a Jack-in-the-box. He gives this to Piglet as a 'friendship present'. To show his thanks, Piglet, along with Tigger and Rabbit, set out to gather honey to give to Pooh in return. Since there is currently a honey shortage in, they decide to travel to the Land of Milk and Honey. Meanwhile, Pooh battles honey-nappers he thinks are stealing honey.
Christopher Robin's mom is insturction her son to clean up his room before he can play outside. The gang realize that this will take far too long. Tigger suggests taking a shortcut and cram it under his bed, which they do. This turns out to be a bad idea as Crud gets grumpy and kidnaps Pooh, Tigger, Piglet, and Christopher Robin.
After waking up and finding his house out of honey, Pooh meets with this friend and discovers that everyone is out of honey. At first, Pooh thinks that he ate all his friends' honey in his sleep, but testimony by Roo reveals a more sinister theory...that there are honey thieves loose in the Hundred Acre Woods. And Pooh got stuck in Gopher's hole.
Rabbit and the gang decide Tigger has jumped into too many mud puddles and therefore must be given a bath. After pinning him down, they are finally able to get him "squeaky clean", but realize, that in the process, washed away his stripes. Confused as to his identity, Tigger sets out to determine who her really is, as he's clearly not a Tigger...or is he?
Christopher Robin is looking for his friends. He wants to see if they want to go to a party. Upon hearing this, they think they forgot Christopher Robin's birthday. They rush to his house and wrap themselves up with bows in an effort to surprise him. While there, they see him carrying a present that "is the best present a kid could get". Curious, they open the box and discover the toy is Bruno the Talking Gorilla.
When Christopher Robin gets a babysitter, he, Pooh, Piglet, and Tigger have trouble falling asleep, and tend to make messes that annoys the babysitter. But when Christopher Robin has to become Roo's babysitter, he learns that babysitting is a much harder job than he thought.
Thinking that he isn't special, Rabbit feels like his friends don't like him. And when Pooh accidentally knocks the days on Rabbit's calendar down, he thinks that everyone forgot his birthday, which leads him on a hectic journey into the town nearby The Hundred Acre Wood.
When a frightening noise leaves Piglet thinking a ghost is on the prowl, Pooh and the gang think that Piglet himself is a ghost when Piglet has a poillowcase over his body. Meanwhile, Tigger helps Eeyore to improve his swinging abilities.
When Pooh tells his friends about Christopher Robin's wishing star, Pooh tries to make his friends' wishes come true since he claims he 'wasted the star' (in reality, the cloud just went over the star when Pooh was looking at it)
It's April Fools Day and the supposed April Fool gives Pooh glue for honey, Piglet fish bowls against his windows, Tigger spotted pajamas and Rabbit a giant carrot balloon. Now to search for this April Fool.
Christopher Robin and his friends have to look after their neighbour dog's, so he can prove to his mother that he can be responsible. The dog rampages through the town, destroying the local supermarket, while trying to direct the dog away with the sound he likes, a honk of a horn.
When Christopher Robin and his friends accidentally break a statue of his great grandfather Eustis while cleaning up (the statue had been in the family for generations), he decides to leave home and set up somewhere else. But it seems he can't move in with anyone from the Hundred Acre Wood.