After Pooh accidentally eats all of the trick-or-treat candy Rabbit collected from the Hundred Acre Wood, Roo and Lumpy set out to capture the Gobloon to wish for more.
He desperately wants to go back, but Roo insists that they should press on, and eventually they find the Slimy Slide, and then the Tree of Terror.
An inspired Lumpy helps Roo set a trap for the Gobloon, but the two hear a sound coming from an old bridge and go to investigate.
Roo finds a Jack-o'-lantern resembling Lumpy, which makes him think his friend has been caught by the Gobloon and turned into a "jaggedy lantern".
Hearing Roo's voice, Lumpy calls for him, but a loud thunder blocks it, prompting him to break his way out of the trap.
The group finally goes trick-or-treating and Kanga, who was the mysterious figure from earlier, throws a Halloween party for the friends and gives them candy, complete with Jack-o'-lanterns she had carved in everyone's likenesses.