Pooh's Heffalump Halloween Movie is an 2005 animated film.
- Jim Cummings - Winnie the Pooh/Tigger
- Jimmy Bennett - Roo
- Peter Cullen - Eeyore
- Ken Sansom - Rabbit
- John Fiedler - Piglet
- Kyle Stanger - Lumpy
It is Lumpy's first Halloween with Winnie the Pooh, Roo, and their friends in the Hundred Acre Wood. The group discusses their plans for Halloween and for their first night of trick-or-treating. Tigger, alarmed by a mysterious figure he spotted earlier in the woods, warns his friends about the dreaded Gobloon, a monster that comes out every Halloween to catch residents of the Hundred Acre Wood and turn them into Jack-o'-lanterns. But Tigger tells them that if the Gobloon is captured first, it will grant its captors one wish. After Pooh eats all of Rabbit's trick-or-treat candy, Roo and Lumpy set out to capture the Gobloon to wish for more candy.
When Roo and Lumpy reach the supposed Gobloon's lair, Lumpy loses his courage to catch the Gobloon. So Roo tells him the story from Boo to You Too! Winnie the Pooh, when Piglet was afraid to go trick-or-treating, but gained his courage. Roo believes that if Piglet can conquer his fears so can Lumpy. An inspired Lumpy helps Roo set a trap for the Gobloon, but the two end up fleeing once they think the Gobloon is returning. After encountering and fleeing from the mysterious figure, Lumpy gets separated from Roo and ends up stuck in the trap they'd set for the Gobloon. Lumpy is heart-broken to be alone, as he and Roo had promised to stay together during the adventure. Roo finds a Jack-o'-lantern resembling Lumpy, which makes him think his friend has been caught by the Gobloon and turned into a Jack-o'-lantern.
Once back with the others, Roo recruits Pooh, Piglet, Tigger, Eeyore and Rabbit to help him capture the Gobloon and save Lumpy. The group arrives at the trap and believes the Gobloon is trapped, unaware that it's actually Lumpy. Roo wishes to have his friend Lumpy back. 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 in reality the mysterious figure that Tigger mistook for the Gobloon, throws a Halloween party for the friends, complete with Jack-o'-lanterns she'd carved in everyone's likenesses. She explains that she must have accidentally dropped Lumpy's Jack-o'-lantern—a mistake that sparked the entire adventure. With Lumpy's first Halloween being successful, everyone from the Hundred Acre Wood enjoys the Halloween party.
- "Trick R' Treating With Our Friends" - Pooh, Tigger, Rabbit, Eeyore, Piglet and Roo
- "Brave Together" - Roo and Lumpy
- "Trick R' Treating With Our Friends (Finale)" - Pooh, Tigger, Rabbit, Eeyore, Piglet, Roo and Lumpy
- "I Wanna Scare Myself!" - Tigger
- "I Am Not Afraid" - Piglet