During a snowstorm, Pooh, Piglet, Tigger, and Rabbit try to salvage a lone carrot in Rabbit's snow-covered garden. When all of a sudden, the gang hears a "Help." It's a baby bluebird in a nest flying around. Rabbit then abandons the carrot to save the bird. Afterwards, Rabbit volunteers to adopt the bluebird, named Kessie. A few days later, Rabbit is feeling the stress of parenthood after trying to take care of Kessie. When Pooh drops by, Rabbit becomes hysterical and manically says that Kessie can play with Pooh and Piglet while he takes care of his garden. While Pooh and Piglet give Kessie a bath, the bird accidentally puts too much soap in the bath. Rabbit, who says that he's going to plant his carrots so early in the year that they'll be ripe by springtime, hears a rumbling coming from inside his house. Kessie is seen inside a soap bubble floating around nearby. Rabbit then runs after her. When Rabbit catches her, he tells her that she shouldn't fly ever again because he doesn't want anything to happen to her. Kessie promises Rabbit that she won't.
Spring arrives, and Rabbit is teaching Kessie how to weed his garden. Rabbit then stubs his toe on a pot that has a carrot in it. Kessie says that was the very first carrot she ever planted. Then Tigger bounces on Rabbit, asking if Kessie can play with him. At first Rabbit refuses, saying that Kessie is busy but he says yes when Tigger messes around with his garden, pulling up all his carrots. While Tigger bounces around the Wood with Kessie, Tigger encounters a very, very tall tree. Knowing that he can't jump over it, Tigger says "I'll embarrass the tree if jump it all at once. So I'll take it in three bounces." But once they get to the top, Tigger and Kessie's weight is too much for the old tree and it begins to shake and fall down. Once it does fall down, Tigger and Kessie find themselves over a very tall cliff. Fearing they are about to fall, Kessie yells for help. Rabbit, who's still working in his garden, hears the yell and immediately rushes over to the fallen tree to try and help. Because Rabbit's afraid of heights, he gets halfway up the tree and stops, saying "I can't move." Meanwhile, Kessie is hanging on for dear life on Tigger's tail who is hanging onto the tree by a branch. Kessie then says that she's slipping. Then Rabbit faces his fear and inches his way across the frail tree. As it tips even more toward the ledge, Rabbit goes back to his original location and the tree evens out. Knowing that if he moves on it could cost him, Tigger and Kessie their lives, Rabbit then tells Tigger to swing Kessie up to him. Rabbit catches Kessie but he doesn't have a strong enough grip and she falls. Rabbit bravely tries to jump after her, but Tigger catches Rabbit saying that it's too late to save her. During Kessie's freefall, Owl arrives and witnesses her falling, telling her a story about his Uncle Horatio. Meanwhile, Rabbit's still on the tree sadly telling Tigger that he never told her that he loved her. But as he's crying, he hears Kessie giggling. Owl is carrying her up to Rabbit, still telling her his story. While the tree is finally going to give way, Rabbit, Kessie and Tigger run off the branch, but Owl stays on and tells Rabbit that Kessie was made for flying, then flies away from the falling tree. Kessie then says that Owl will teach her to fly, and he says it will be his pleasure and that with a little practice and she'll be able to fly south for the winter. This deeply troubles Rabbit and out of an act of love says that Owl will never teach Kessie how to fly. As Rabbit walks away with Kessie in his hands, she informs him that she has wings and that she can fly. But Rabbit tells her that flying leads to no good and reminded her of her promise.
Later in the day, Rabbit is reading Kessie a story. But Kessie is still sad that she's not allowed to fly even though it's her dream to do so. In the middle of the story, Kessie walks away, looks out the window and sees other birds flying. Then as spring gives way to summer and summer to autumn, Kessie is walking around the woods without Rabbit and is still saddened by the fact she can't fly. Seeing a flock of birds, Kessie decides to climb up a tree and try to fly. But she just falls into a pile of autumn leaves. Trying again, only this time higher in the tree, she fails again and lands right on top of Pooh Bear. She informs Pooh not to tell Rabbit about her flying attempts because it'll make him so sad. Pooh then says he'll help teach her to fly, saying she's great at going down, but just needs to learn to go up. Then Pooh takes her to a great, big cliff and while Piglet ties a slingshot to two trees at the end of the cliff, Pooh, Piglet and Tigger pull back on the slingshot with Kessie inside the slingshot. But just before Kessie could take her maiden voyage, Rabbit interrupts it and angrily tells Pooh that she's not flying. Then he steps inside the slingshot and yells at Pooh, saying "You're teaching Kessie to fly, and against my wishes." Rabbit then grabs Kessie away from Pooh's arms and feels betrayed, but Kessie says she has to fly and that it means everything to her. Tigger, who's still pulling on the slingshot then tells Rabbit that he should "give the kid a chance." Rabbit, still inside the sling, tells Tigger to stay out of the conversation and to let go of the slingshot. Although Tigger protests, Rabbit pulls the slingshot out of his hands not knowing that he's going to get pulled forward by the slingshot and because Rabbit can't fly, he falls off the cliff. Kessie then runs off the cliff and tries to save him. During Rabbit's freefall, he braces himself for the not-so-smooth landing. Then Kessie pulls Rabbit up the ledge with his friends. While Pooh, Piglet, and Tigger celebrate over Kessie's achievement, saying that she flew excellently and that she can now fly south for the winter, Rabbit walks away sadly, knowing that he's going to lose Kessie, maybe forever.
Later that night, Rabbit is on his rocking chair nearby the fireplace looking at Kessie's favorite stuffed animal. Kessie then walks into the room and asks Rabbit to read her one last bedtime story. Rabbit then walks away, gloomily saying "You don't need me to read you a bedtime story... You don't need me for anything." After Rabbit departs, Kessie sits by the fireplace in her chair and cries. Then Rabbit is in his room and the camera pulls out to reveal the Hundred Acre Wood in a fresh blanket of snow.
The next morning, Piglet, Pooh, Tigger, and Owl are giving Kessie one last lesson in flying. But Rabbit is absent from the event, and Kessie says she can't leave without saying goodbye to him. Meanwhile, Rabbit's in his snow-covered garden searching for that first carrot that Kessie planted. While the gang say their last goodbyes, Rabbit does find the carrot then races against time to say goodbye to Kessie. But Rabbit is too late, Kessie is already airborne before he gets a chance to say goodbye, saying "I've change my mind! You can fly... just don't go away, Kessie." Realizing that he'll probably never see Kessie again, he drops her carrot over the cliff and sadly sits on a rock nearby. But then Rabbit hears Kessie's laugh and sees her carrot fall out of the sky, and he is happy to see her when she comes back for him. Kessie then says, "Did you think I would leave without saying goodbye to you?"
In the final scene of the episode, Pooh and Piglet are sitting by the enchanted place on top of the forest looking at the sunset. Piglet then mentions to Pooh that for the longest time, he thought Rabbit didn't like Kessie. However, Pooh says that when you care about someone too much, it's called love. Piglets then asked Pooh if they should tell Rabbit that, to which Pooh says not to worry, because he already knows. The episode ends with a shot of Rabbit staring out to the sky with Kessie's carrot at his side, waiting for Kessie to return in the Spring.