An adult Christopher Robin, who is now focused on his new life, work, and family, suddenly meets his old friend Winnie the Pooh, who returns to his unforgotten childhood past to help him return to the Hundred Acre Wood and help find Pooh's lost friends.
Winnie the Pooh and Christopher Robin are best friends who wish they could be together forever. However Christopher Robin needs to go to school. Christopher Robin has trouble telling Pooh that they will be separated, so he leaves him a note. Pooh, misunderstanding and believing that Christopher Robin has gone to Skull and needs his help launches a rescue mission with the help of Rabbit, Tigger, and Piglet.
A heffalump is heard trumpeting in the hundred acre woods. Winnie the Pooh, Tigger, and Piglet are scared and rush to Rabbit's house for advice. Roo joins them and they all agree that heffalumps are nearby after finding a huge footprint. They decide to set out on an expedition to catch the heffalump. Roo is not allowed to come along because he is too little.
Disney's animated classic takes on a new form, with a widened mythology and an all-star cast. A young prince, imprisoned in the form of a beast, can be freed only by true love. What may be his only opportunity arrives when he meets Belle, the only human girl to ever visit the castle since it was enchanted.