The story begins with Tigger wanting to ski, but Winnie the Pooh and Piglet point out that there’s no snow. So, they go ask Rabbit what day of the year it is, but after opening his front door and letting the wind blow in, Rabbit’s calendar pages (November to February) get torn off and get swept under Rabbit’s bed, but he doesn’t realize it, and claims that it’s February 2, Groundhog Day. In an effort to find out if there are two more weeks of winter or if spring comes tomorrow, they ask Gopher if he sees his shadow. Gopher angrily points out he’s a gopher not a groundhog, so they have Piglet pretend to be a groundhog. His hat falls over his eyes, preventing him from seeing. Thinking that winter is over, they all prepare for spring by airing out their houses, planting gardens and spring cleaning. Piglet returns home, feeling happy about telling his friends that winter is over, but later that day, it snows. Tigger is puzzled to see that it’s snowing during spring while snow is being blown into Pooh’s house. A discouraged Rabbit confronts Piglet for lying to them and tells him that it’s all his fault, and goes home to see wind blowing into his house and the calendar pages being blown outside. After putting the lost pages back on the calendar, he realizes that it’s not Groundhog Day, it’s only November 13. Feeling awful for what he said, Rabbit goes to apologize to Piglet, only to find a note from Piglet saying that he’s gone to look for a real groundhog. Rabbit frantically goes looking for Piglet. Meanwhile, Piglet can’t find a groundhog, and decides to go home after a pile of snow falls on him, and he leaves his hat behind on the pile of snow. Rabbit finds the pile of snow. Thinking that it’s Piglet frozen solid, he rushes to Pooh’s house, where he, Tigger and Pooh melt the snow. Thinking that Piglet has melted, Rabbit solemnly cries, and apologizes for everything, only to realize that the real Piglet is behind him and the melted snow was just a normal pile of snow. Rabbit tells everyone that it’s November 13. So, they decide to get ready for Thanksgiving.
A month later, on Christmas Eve, Rabbit tells the story of how he met a baby bluebird named Kessie. Later that summer, Owl teaches her to fly. Rabbit refuses to let her fly, and with that, they go home. In the fall, Kessie looks out the window to see wild ducks flying South for the winter. For days, she tries to fly, but is discovered by Pooh, who promises not to tell Rabbit. Pooh, Tigger, and Piglet have an idea on how to get Kessie South for the winter, a giant slingshot. When Kessie is about to take off, Rabbit arrives, and stops him. He yells at Pooh, and tells Tigger to let go of the slingshot. Tigger lets go, and Rabbit is hit, and falls off the same cliff Kessie had fallen off of that summer. Kessie quickly swoops down, and grabs Rabbit, and brings him back to the top. The next morning, Owl, Pooh, Piglet, and Tigger say goodbye to Kessie as she prepares to fly South. Meanwhile, Rabbit is in his garden feeling sad, and stubs his toe on a potted carrot, that Kessie had planted. He rushes to say goodbye to Kessie, but finds he’s too late now and Kessie is gone. However, he is happy when Kessie comes back to say goodbye. Later that day, Pooh and Piglet are relaxing by Christopher Robin’s favorite tree talking about how Rabbit loved Kessie, and how they can’t wait to see her again. Back in the present, Rabbit tells Roo that he hasn’t seen Kessie since then, as Tigger cries. Rabbit looks at his clock to see that it’s getting late, and hurries everyone outside to decorate a tree. Christopher Robin arrives to help decorate. After the tree is done, Rabbit realizes he forgot the most important part, a star to go on top of the tree. Rabbit is really sad, but then sees a falling star. Everyone gathers to make a wish, only to realize that it’s not a falling star, it’s Kessie holding a star, which she puts on the tree. Rabbit and Kessie hug, and Kessie wishes Rabbit a Merry Christmas, ending the story.