When Lord Cucuface, head of Madeline's school, takes a telescope from the attic during a surprise inspection, its ghostly owner convinces Madeline to help get it back, with help from neighbor Pepito and her fellow orphans.
When Drake discovers that his friend and fellow Dragon Master, Bo, is trying to steal the Dragon Stone, he wonders if the dark wizard might be behind it, and he must try to find a way to protect the stone while keeping Bo's family out of danger.
Kaya, Anna, and Reed hope their pumpkin, Herbert, will take home first prize at the Windy City Pumpkin Fest, but when Herbert suddenly disappears, the friends must catch the thief in time for the festival.