It's Halloween in the Hundred-Acre-Wood, and everybody is excited for the holiday - everybody except Eeyore, that is, who doesn't care for sweets, costumes, parties, and doesn't think there's anything worth getting scared of. While the others prepare for a party, Eeyore tries to find peace and quiet on Halloween, taking him on an adventure all the way to the Scary Woods.
The Book of Boo contains examples of:
- Actually Pretty Funny: Eeyore admits that a good scare in a safe environment with his friends is actually pretty fun.
- Chekhov's Gun: Piglet's side-plot regarding wanting to find the scariest costume comes into play at the end when he is the one who surprises and scares Eeyore.
- "Could Have Avoided This!" Plot: Eeyore could've avoided his journey to the Scary Woods if he had kept his house off explicitly used pathways to Kanga's house, considering there's a whole Wood for him to use.
- Drunk on Milk: Rabbit is seen hiccupping and looking intoxicated even though, given the show's target demographic, he can't be drinking anything other than normal punch.
- Halloween Episode: The only episode of the series revolving around Halloween, and to date, the second Halloween-focused installment of the franchise since Boo to You Too! Winnie the Pooh.
- My God, What Have I Done?: Rabbit becomes hysterical at the party once he remembers Eeyore was heading for the Scary Woods since his interference caused Eeyore to pack up and head there.
- 1-Dimensional Thinking: Eeyore, when trying to move his house out of the swamp, keeps putting his house on explicitly used pathways to Kanga's house when he could've just moved it off the pathways.
- Sure, Let's Go with That: Kanga awards Piglet the award for scariest costume calling him a "rock goblin", since he's still wearing his mountain costume that got mucked up from going through the mud and brush of the Scary Woods. Piglet doesn't object, too happy he got the award to begin with.
- Tempting Fate: The other characters spend the whole episode warning Eeyore that being too haughty about Halloween will result in him getting scared like the goose in Owl's story, and by the end of the episode Eeyore admits it as well.
- Took a Level in Badass: In the previous Halloween special based on the franchise, Piglet had to get over his fears of the holiday. In this episode, he's happy to participate in the holiday with his friends and actually wants to be the one wearing the scariest costume.
