Voiced by: Kirk ThorntonThe main protagonist. After a car crash, he loses his young daughter Cheryl and will stop at nothing to find her, no matter what abominations he must face.Turns out, he has been dead for years and may or may not be a figment of Cheryl's imagination, a "perfect" idea of her father she created after the guilt of his death.
Cheryl MasonHarry's young daughter, gone missing after he crashed his car. Harry's goal is to find her, no matter what.She actually never was in the crash, which happened 18 years ago, that killed Harry. The therapy sessions in the game are via her perspective.
Cybil BennettA cop who flip-flops between helping or hindering Harry, and will act and dress differently depending on how you act in the game and answer the questions in the therapy session.
Dahlia MasonA woman who mysteriously pops up in the game midway, who hits on Harry as if she was his lover, despite Harry having no clue who she is. Her clothes and attitude are affected by in-game choices and the therapy sessions.In reality, she is Harry's ex-wife and Cheryl's mother, who Cheryl resents heavily.
Michael KaufmannThe therapist that is seen in the first-person therapy sessions. He is bitter and pessimistic about marriage and love.
Michelle ValdezA former student/prom queen of Midwich High School and the sole attendee of the high school reunion (canceled due to the snow storm). She claims that she attended school with Cheryl Mason. She is currently dating a guy, but he either breaks up with her, or vice versa, depending on player actions. Her outfit changes depending on the in-game actions and the answers in the psychological parts of the player.One of the endings implies that Harry was having an affair with Michelle, along with Lisa, behind Dahlia's back.
Lisa GarlandA nurse at the hospital in Silent Hill. One of the endings implies that Harry was having an affair with Lisa, along with Michelle, behind Dahlia's back. She dies, though it may or may not be the player's fault, depending on the player's actions.