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On Halloween evening, everyone gathers at Owl's house and listens to a spooky story from The Book of Boo. Everyone is thrilled and spooked by the story except by Eeyore, who seems to find the story rather boring and says nothing much scares him. He says that he doesn't understand all the fuss about Halloween and heads for home. Later everyone heads for Kanga's house for a Halloween party and some people keep knocking over Eeyore's house on the way there where Winnie-the-Pooh and his friends from the Hundred Acre Wood dress up in costumes for kangas halloween party while Eeyore moves to the scary woods. until irritated, Eeyore says he's moving to The Scary Woods because he knows nobody else goes there, but he's not scared. Where eeyore chose to move his house of sticks into the scary woods because it kept on getting knocked over he was sure that it would be safe in the scary woods as normally everyone else was afraid to go in there where piglet went to seach for eeyore in the scary woods until he finds himself a chance of winning it until tigger finds his usual buoyant personality getting scared when he is in owls scary treehouse with rabbit where piglet gets worried about the costume contest.
On the side of the story, at the party there was a costume contest, the contestants were:
- Little Red Riding Hood - Pooh
- Wolf - Tigger
- Flower - Eeyore
- Witch - Kanga
- Bat - Kessie
- Wizard - Owl
- Mountain - Piglet
- Ladybug - Rabbit
- Ghost - Roo
Winner: Piglet, for scaring Eeyore where piglet wins the scariest costume contest after his costume becomes covered in leaves and he scares eeyore Eeyore initially chooses to not to wear a costume but dons one after getting scared by piglet
- I Wanna Be Scary
- Nothin' Much Scares Me
- The Hundred Acre Halloween