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. Rabbit's calendar pages blow away, 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. He can't see through his mask, so they all prepare for spring by airing out their houses, planting gardens and spring cleaning. But, later that day, it snows. Rabbit confronts Piglet and tells him that it's all his fault, and goes home to see that his calendar pages are on the floor, and 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 ice. Thinking that Piglet has melted, Rabbit cries, and apologizes for everything, only to realize that the real Piglet is behind him. Rabbit tells everyone that it's November 13,. So, they decide to get ready for Thanksgiving.
When Thanksgiving arrives, Pooh is at his house, when Christopher Robin arrives, and they talk about the celebration at Rabbit's house later that day. Pooh then dances around the Hundred Acre Wood Everyone, except Christopher Robin, arrives at Rabbit's house with food that they each brought. Rabbit tells everyone that what they brought is not a traditional Thanksgiving dinner. He assigns Owl to wash the dishes, Gopher to make the pumpkin pie, Tigger and Eeyore to pick cranberries, and most importantly Pooh and Piglet are to get the turkey. Gopher literally blows up a pumpkin to make the pumpkin pie. Tigger and Eeyore gather up cranberries, while Tigger sings a silly song about berries. But, on their way back to Rabbit's house, they realize that there's a hole in their sack, and go to pick some more cranberries, only to fall into Pooh and Piglet's turkey trap. Thinking that they've captured a turkey, Pooh and Piglet take the sack to Rabbit. Gopher arrives with the pie, and sits it on the table next to the sack that Tigger and Eeyore are in. Everyone is scared to open the sack, but Tigger and Eeyore brake out, and Tigger accidentally throws the pie, but then Rabbit catches it, only to have Tigger scare him, and it hits him in the face. Everyone disappointedly goes home. Pooh realizes that if they all share the food they originally brought, they can have a great Thanksgiving. So, he gathers up everyone, and they surprise Rabbit with the Thanksgiving dinner they've set up. They are joined by Christopher Robin, who proposes a toast, with lemonade, to the best Thanksgiving celebration ever.
A month later, on Christmas Eve, everyone, except Christopher Robin and Gopher, are at Rabbit's house decorating. Roo is worried that Santa won't like his cookies, but Kanga assures him that Santa will love his cookies. Tigger arrives with a special delivery from Kessie, a bird that Rabbit took care of. Roo is curious and asks who Kessie is. So, Rabbit tells him the whole story. Rabbit, Tigger, Piglet, and Pooh Bear are desperately trying to save a carrot during a blizzard. They hear a cry for help, and see a baby bluejay hanging onto a tree. Rabbit begins to panic, and rushes to his house to get a ladder. But because of the wind, Rabbit, Piglet, Tigger, and Pooh end up flying on Rabbit's front door. Rabbit catches the bluejay in Pooh's hunny pot, and they crash into Rabbit's house. Rabbit decides to take care of the baby bluejay, who calls herself Kessie, himself. After a mishap with a bath that Pooh and Piglet gave her, Kessie winds up in a bubble, and when it pops, Rabbit catches her, and tells her to never go up so high again. In the summer, an older Kessie holds onto Tigger's back, while he bounces onto a large tree, which falls, leaving Kessie and Tigger hanging on for dear life. Rabbit arrives to help, but Kessie slips from Rabbit's hand, and plummets off the cliff. Rabbit tries to go after her, but Tigger manages to get off the tree and stop him, telling Rabbit that Kessie is gone. Meanwhile, Kessie is still plummeting and Owl arrives and tells her to flap her wings. Back on top of the hill a tearful Rabbit sadly says that he never told Kessie that he loved her. Kessie and Owl arrive, and Kessie and Rabbit hug. Kessie tells Rabbit that Owl is going to teach her how to fly. Rabbit refuses to let her fly, and with that, they go home. In the fall, Rabbit is reading Kessie a story about a princess, and a knight. Kessie looks out the window to see other birds flying South for the winter. She announces that she's going to go outside. For days, she tries to fly, but is caught 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 her. 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. Now that Kessie can fly, she plans on going South the next day. That night, Rabbit is sadly looking at Kessie's stuffed bunny. Kessie asks Rabbit to read her one last bedtime story, but Rabbit claims that Kessie doesn't need him for anything, and goes to bed. Kessie cries all night. 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 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. They look down below them to see Rabbit sitting by another tree. Back in the present, Rabbit tells Roo that he hasn't seen Kessie since then, as Tigger sobs. 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.