It's Halloween in the 100 Acre Wood, and Roo's best new friend, Lumpy, is looking forward to his first time trick-or-treating. That is, until Tigger warns them about the scary Gobloon, who'll turn them into jack-o'-lanterns if he catches them. But if Roo and Lumpy turn the tables on the Gobloon, they get to make a wish! Lumpy and Roo decide to be "brave together, brave forever" and catch the Gobloon so they can make their wishes come true.
Kronk, now chef and Head Delivery Boy of Mudka's Meat Hut, is fretting over the upcoming visit of his father. Kronk's father always disapproved of young Kronk's culinary interests and wished that Kronk instead would settle down with a wife and a large house on a hill.
When Rabbit is named Mayor of the Hundred Acre Wood, the position goes to his head and he starts making crazy rules, including one that forbids Tigger from bouncing. Everyone in the wood must choose sides, until a little girl loses her dog Buster and everyone must join together to find him.
Pooh and his friends work together to rescue Santa's lost reindeer-trainee, Holly.
During an ordinary day in Hundred Acre Wood, Winnie the Pooh sets out to find some honey. Misinterpreting a note from Christopher Robin, Pooh convinces Tigger, Rabbit, Piglet, Owl, Kanga, Roo, and Eeyore that their young friend has been captured by a creature named "Backson" and they set out to save him.
