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 and for their first night of trick-or-treating. Tigger then describes Halloween in a song that results in Tigger knocking on the door, sneaking up on Rabbit, wearing his apron like a cape, spinning ghost streamers around in the air, and Halloween decorations moving along with ghostly howls. Lumpy is scared by Eeyore in a Halloween mask and hides under the table in which Piglet later wonder if spookables are also hiding under the table causing Lumpy to run out. Roo takes a ride on a Halloween basket and Lumpy is hit by a pumpkin headed ghost (which is Roo). Tigger then cuts out ghost shapes on a lampshade and spins it around on the lamp to make it look like real ghosts. Pooh then spills water on the lamp knocking off the shade and putting out the fire. Tigger then turns on a flashlight and says "boo" causing Lumpy to hide under the bed. Roo is so excited to introduce Lumpy to Halloween, and Lumpy looks forward to celebrating Halloween. Until Tigger warns them about the Gobloon, a monster that appears every Halloween to search for the residents to catch and will turn any unsuspecting victims into Jack-o-lanterns (pronounced "Jaggedy-Lanterns" by the characters) if he catches them, but if the gobloon is captured before he catches them first, the Gobloon will grant its' captors one wish. When Pooh eats Rabbit's entire stock of candy for trick-or-treating, Rabbit lets everyone know the bad news Pooh Bear ate all the candy that Rabbit had already gathered and states that there is no more candy in the Hundred Acre Wood. Meanwhile, Roo and Lumpy set out to capture the Gobloon to wish for more candy. Meanwhile according to Tiggers directions they are able to go past the Creepy Cave then down the Slimy Slide and into the Tree of Terror later on Entering the Creepy Cave, Lumpy and his lunchbox get stuck on some rocks, Which leads Lumpy to believe that they're being followed. 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.
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). In the beginning of this story Piglet faces his fears about halloween in order to celebrate it with his best friend Winnie the Pooh. But when his Friends show up at his house Piglet still has not picked a halloween costume and eventually he decides not to participate it And so with the entire holiday falling apart each of them return to their perspective home but later they decide to spend the evening however Piglet runs away into the forest at the first sight of his costumed friends lost in the woods where upon seeing Pooh in the tree, with Eeyore and Tigger (dressed up as Spookables) trying to get him down Piglet decides to rescue him, And then they all end up rolling right through Rabbit's well-kept pumpkin patch. But, this means that Piglet has conquered his fears of Halloween became unscared. And enjoys Halloween with all his friends. Meanwhile at the end of this story Lumpy recovers his courage and helps Roo set a trap for the Gobloon, but the two end up running away when they know that the Gobloon is 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 whole adventure. Later at Piglets House Scarecrow Rabbit, Superhero Tigger, Honeypot Pooh Bear and Bandit Eeyore have decided that instead of Halloween candy, they'll have vegetables for Halloween, and they all go trick or treating At each others houses. Where Roo ends up back in the Tree of Terror himself and Roo finds a Jack-o'-lantern resembling Lumpy, which makes him think his friend has been caught by the Gobloon. Where he vows never to leave Lumpy again as he goes and warns the other trick or treaters.
Meanwhile 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, 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. Where there isnt one for Lumpy as she explains that she must have accidentally dropped Lumpy's Jack-o'-lantern--a mistake that sparked the entire adventure. And so with Lumpy's first Halloween being successful, everyone from the Hundred Acre Wood enjoys the Halloween party. and has fun on his first halloween where Lumpy now loves Halloween as Pooh prepares a candied apple and everything is once again grand.
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 on June 25, 2005.
This is also the last Pooh Film in which Ken Sansom provides Rabbit's voice, though this is not the last time Sansom voiced Rabbit. Sansom's final work as Rabbit was in the recent Pooh series My Friends Tigger & Pooh. Sansom died on October 8, 2012 due to a stroke.
Travis Oates did Piglet's voice in some scenes but he appears on the Additional Voices.
Nikita Hopkins the voice of Roo was replaced by Jimmy Bennett.