After flying a kite, Pooh is eager to figure out how to fly. Pooh's friends are not happy with this when Owl says that the only way for Pooh to fly is by breaking the law of gravity. When Pooh supposedly flies (being hung from a tree), he is locked up in his room for breaking this law!
One spring day, Christopher Robin takes Pooh and his friends to fly his kite. While doing so, Pooh imagines how nice it must be to fly himself. He is so deep in thought that he makes the kite fall to the ground. When the others ask what made him so distracted, Pooh admits his dreams to fly, to which his friends laugh hysterically at him. Eeyore, however, volunteers to help Pooh fly.
First, Pooh coats himself in feathers and glue and tries to fly, but falls down a cliff and ends up landing on Rabbit, who is floating by in an innertube. Rabbit is surprised that Pooh's still trying to fly. Pooh's next attempt is to use roller skates, and is pushed off of a hill by Eeyore. It seems to work for a bit, though not for long.
Meanwhile, Rabbit has gathered Piglet and Tigger to discuss Pooh's desire to fly. After being knocked into his garden river, Rabbit takes them to Owl's place, knowing he will know for sure if Pooh can fly. Sure enough, Owl explains that Pooh does not have the requirements to fly, and the only way he can is if he breaks the law of gravity. The others are horrified at the idea of breaking the law.
Eeyore attaches Pooh to a kite as their next attempt to get Pooh into the air. Eeyore has the kite attached to a tricycle, and rides it down a hill to give Pooh off of the ground. He is "stopped" by Piglet, Rabbit, and Tigger, and Pooh's kite is found caught in a tree. The others, however, think Pooh has actually done it and broken the law of gravity.
As a punishment for breaking the law, they send Pooh to his "room", having turned his house into a prison cell. Rabbit claims he must stay in the cell for 2-3 hundred years. However, Piglet doesn't want Pooh to be lonely in that time, and insists he stay with him. Tigger obliges and puts Piglet in the cell. Eeyore comes by, saying he is partially responsible for making Pooh fly, making Tigger push him into the cell as well. Owl then reveals he feels responsible for what happened, so Tigger locks him up as well. Rabbit decides to leave with Tigger, though says he should have stopped Pooh when he had the chance. Hearing this, Tigger locks up Rabbit, and is about to leave when Pooh starts sharing his honey with them, starting a little tea party. Tigger overhears and declares that they can't have fun without him (having fun's what tiggers do best)!
When Christopher Robin returns, he find them all in the cell. Pooh explains that he is in for breaking the law of gravity. Christopher Robin lets them out and explains that trying to fly isn't against the law; it's just impossible. He tells Pooh that if he were to fly, the bees wouldn't stand a chance, and would not be able to make honey. Hearing this, Pooh gives up on trying to fly, deciding to leave that to the bees. While the others thank Christopher Robin for talking Pooh out of flying, Eeyore sees Pooh attempting to fly again. This time, however, Pooh manages to succeed for a few seconds. Eeyore says that he knew Pooh could do it as he watches Pooh "fly" off.