One winter day Christopher Robin rushes off to go play with his friends in the snow, but not before his mom tells him to wear his earmuffs while going out. When Christopher Robin meets up with Pooh and Tigger, Pooh asks why Christopher Robin must always wear his earmuffs, to which Tigger replies his toes will get cold. Christopher Robin says that he has to wear them because of his Mom's overprotection of him.
Christopher Robin then pushes their sled and then the 3 go sledding off into the snow, eventually bumping into Piglet, who lands in Pooh's arms. When Piglet asks where they're going, Pooh says they are going skating. On the ice Pooh, Tigger, and Christopher Robin join Rabbit, Owl, and Eeyore for skating while Gopher fishes nearby, but Piglet is too afraid to step on the ice. Then Roo shows up and asks if anyone wants to play ice cookie, and Christopher Robin asks if he was referring to ice hockey. Roo tells him that the name has to be changed because he's out of hockey pucks and his mama gave him an oatmeal cookie.
Tigger and Christopher Robin decide to be the captains of the 2 teams, and Tigger picks Roo, Eeyore, and Owl for his team while Christopher Robin chooses Pooh, Rabbit, and Piglet for his team but Piglet rejects and runs away, telling his friends he has to mow his lawn. While the 2 teams play the game, Pooh finds Piglet up a tree and ask him why he's up there, to which Piglet replies, "I can't skate." Then the tree branch breaks and Piglet lands on the ice cookie and Rabbit hits it into the snow. Afterwards Christopher Robin comes forward and asks Piglet what's wrong, and Pooh tells him that Piglet can't skate and feels ashamed about it, so Christopher Robin and the others decide to teach him. First they try putting small skates on Piglet and it almost works, but Piglet loses his balance once Christopher Robin lets go of him and falls down into Gopher's fishing hole.
Second, Tigger tries to put big skates on Piglet's feet and when he pushes Piglet from behind Piglet goes skating pretty fast and flies upside down in the air and lands in the snow. As the gang tries to figure out what to do next, Pooh says that maybe Christopher Robin's earmuffs might work, so Christopher Robin puts his earmuffs on Piglet's ears and then he and Pooh take Piglet to a small pond. Piglet finally can skate well and tells his friends that he can't wait to play Ice Cookie, but Pooh says the game is now called Ice Honey because Eeyore ate the cookie puck and Rabbit brought a honey jar to use as a replacement puck. He and Christopher Robin run off to play in the game, leaving Piglet to skate on his own.
After the game Owl and Christopher Robin leave to go home but Pooh, Rabbit, Tigger, and Roo stay behind. Pooh notices Rabbit's honeypot on the ice and wonders if there's any honey left in it. He accidentally goes onto the ice without skates and his friends follow him, then the ice breaks into water causing the gang to be trapped on an iceberg. Piglet hears his friends' screaming and comes to their rescue. He grabs their skates and throws them to them but then the earmuffs fall of Piglet's head and land in the water and he chases them while his friends make it safely to shore. On shore, the friends watch frighteningly as Piglet catches the earmuffs and almost goes over the waterfall, but manages to run back up and back across the icebergs and lands in the snow. Later the gang watches Piglet skate on the small ice and they realize he doesn't need the earmuffs after all.