Lumpy's first Halloween with Pooh, Roo, and their friends in the Hundred Acre Wood. The group talks through Halloween plans and the excitement of their first night of trick-or-treating. Tigger chimes in with the tale of the Gobloon, a spooky monster that appears each Halloween to hunt someone down and turn them into jaggedy lanterns; but if the Gobloon is captured first, it will grant its captors one wish.
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 and wish for more. Following Tigger's directions on the map, they travel past the Creepy Cave, then down the Slimy Slide, and into the Tree of Terror. At the Creepy Cave, Lumpy's lunchbox gets stuck on the rocks, which makes him fear they are being followed. He desperately wants to turn back, but Roo encourages them to press on, and eventually they reach the Slimy Slide and the Tree of Terror.
When Roo and Lumpy reach the Gobloon’s supposed lair, Lumpy loses his courage and wants to go home. So Roo recounts the story from Boo to You Too! Winnie the Pooh, where Piglet faced fear and found courage. Inspired, Lumpy helps Roo set a trap for the Gobloon, but a sound from an old bridge makes them pause to investigate.
After encountering and briefly fleeing from a mysterious figure with a wheelbarrow full of Jack-o'-lanterns, they realize they’ve been misled. Lumpy gets separated from Roo and ends up trapped in their own trap. He is heartbroken to be alone, since Roo had promised to stay together. Roo finds a Jack-o'-lantern that looks like Lumpy, and fears his friend has been caught by the Gobloon and turned into a jaggedy lantern.
Returning to the others, Roo pleads for help as the group—Pooh, Piglet, Tigger, Eeyore, and Rabbit—organizes a rescue. Pooh and the others, who had been using vegetables since Pooh had eaten all the candy, rush to the trap and believe the Gobloon is trapped. Roo wishes for Lumpy’s return, but the Gobloon does not grant the wish. A shout from Roo sounds through the area, but a loud thunderclap blocks it, and Lumpy breaks free from the trap. The two friends are happily reunited.
With the danger over, they head out for Halloween trick-or-treating. Later, Kanga throws a Halloween party and shares candy, including Jack-o'-lanterns carved in everyone’s likeness. Although Lumpy’s Jack-o'-lantern was not present, Kanga explains she made one but must have dropped it, which turns out to be the Jack-o'-lantern Roo found. The first Halloween in the Hundred Acre Wood ends on a joyful note as everyone enjoys the party together.
