It's Halloween in the Hundred 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.
| Actor | Role |
|---|---|
 Jimmy BennettRoo (voice) | Roo (voice) |
 Peter CullenEeyore (voice) | Eeyore (voice) |
 Jim CummingsPooh/Tigger (voice) | Pooh/Tigger (voice) |
 John FiedlerPiglet (voice) | Piglet (voice) |
 Ken SansomRabbit (voice) | Rabbit (voice) |
 Kath SoucieKanga (voice) | Kanga (voice) |
| KKyle StangerLumpy (voice) | Lumpy (voice) |
 David Ogden StiersNarrator | Narrator |
 Travis OatesAdditional Voices (voice) | Additional Voices (voice) |
 Nikita HopkinsRoo (voice) | Roo (voice) |
 Michael GoughGopher (voice) | Gopher (voice) |