Urban legends is a form of folklore popular in Hillwood, especially among children. Gerald is considered the keeper of the urban legends, he is a skilled legend-teller. Most likely he learns the urban legends from his mysterious informant Fuzzy Slippers. Most of the legends turns out to be based on actual facts.

List of Urban legends:

• Legend of the Ghost Bride
• Legend of the Haunted Train
• Legend of the Headless Cabbie
• Legend of Monkeyman
• Legend of Pidgeon Man
• Legend of Stoop Kid
• Legend of Wheezin' Ed