As a reward for Christopher Robin eating all his vegetables, he along with Pooh, Piglet, and Tigger go to the theater to watch Birdzilla, a scary monster movie. During the film, Piglet gets scared and thinks the movie is real and the monster will get him. The gang tries to convince him that it is only make-believe and proceed to make their own monster film to prove it.

Christopher Robin gives Piglet "magic earmuffs" to help give him confidence in his ice skating. After losing the earmuffs, Piglet has a crisis of belief, only to discover his own skill when he must save the gang from the perils of an icy river.

When the gang discovers that Tigger has never had a birthday, they decide to throw him a party that fails to impress him, especially when he does not get what he wants. A trip to the Hundred-Acre-Wood's wishing well leads Tigger to "Wishland," where everything he desires comes true. Eventually, though, he must choose between all of the possessions he has gained and his friends.