Guest Stars Ridge Canipe as Young Dean Winchester Colin Ford as Teenage Sam Winchester Spencer Garrett as Edward Carrigan Merrilyn Gann as Madge Carrigan Co Starring Emily Holmes as Mrs. Walsh Jennifer Copping as Mrs. Caldwell Victoria Bidewell as Molly Johnson Douglas Newell as Grandfather Alex Bruhanski as Santa Village Santa Connor Christopher Levins as Jimmy Caldwell Zak Ludwig as Stevie