It is Lumpy's first Halloween with Roo, Winnie the Pooh and their friends in the Hundred Acre Wood. While the group discusses their plans for Halloween, Tigger tells the story of the Gobloon, a monster that will turn its' prey into Jack-o-lanterns (pronounced "Jaggedy-Lanterns" by the characters), but if it is captured, the Gobloon will grant its' captors one wish. When Pooh eats Rabbit's entire stock of candy for trick-or-treating, Roo and Lumpy set out to capture the Gobloon to wish for more candy.
Lumpy's courage fails him when they reach the Gobloon's supposed lair, so Roo tells him the story of when Piglet gained his courage (the "Boo to You Too, Winnie the Pooh" special). Inspired, Lumpy helps set a trap for the Gobloon, but the two end up running away when they believe the Gobloon to be returning. Lumpy is separated from Roo, the latter fleeing from an unknown figure with a wheelbarrow full of pumpkins. Lumpy ends up caught in the trap they had for the Gobloon. Lumpy is heart-broken to be alone, as he and Roo had promised to stay together during the adventure.
Roo recruits Pooh, Piglet, Tigger, Eeyore and Rabbit to help him capture the Gobloon and save Lumpy. The group arrives at the trap and, hearing Lumpy trying to break out of the trap, assume the Gobloon was trapped already. The group is unsure what to wish for, but Roo wishes to have his friend back. Hearing Roo's voice, Lumpy is inspired to finally break his way out of the trap, much to the joy of his friends. The group finally goes trick-or-treating, and Kanga, who was in reality the mysterious figure, throws a Halloween party for the friends, complete with Jack-o-lanterns carved in everyone's likeness.
- Narrated by David Ogden Stiers
- Jimmy Bennett as Roo
- Kyle Stanger as Lumpy the Heffalump
- Peter Cullen as Eeyore
- Jim Cummings as Winnie-the-Pooh and Tigger
- John Fiedler as Piglet
- Ken Sansom as Rabbit
- Kath Soucie as Kanga
- Travis Oates as additional voices
- Michael Gough as Gopher (uncredited)
- Nikita Hopkins as Roo (uncredited, a few scenes only)
- Christopher Robin and Owl are still absent in this film. Gopher only appears during the Boo to You Too sequence, but is otherwise excluded from all scenes.
- To date, this is the last in Disney's Winnie the Pooh media line to feature Gopher, although the Beaver in My Friends Tigger & Pooh loosely resembles Gopher.
- This is the last Pooh film in which John Fiedler provides Piglet's voice, due to his death from cancer in 2005.
- Travis Oates did Piglet's voice in some scenes but he appears on the Additional Voices.