Heather Mason / Sharon Da Silva
- Played by Adelaide Clemens
- Action Girl: Carries a gun with her during Silent Hill and willingly takes on several monsters and the Leonard monster to retrieve the Seal of Metatron.
- Action Survivor: As opposed to Silent Hill 3's Heather, who is more of an Action Girl.
- Apocalypse Maiden: The Order of Valtiel intend to use Heather's body as an incubator for their unborn god. Turns out Claudia's side of the Order wanted Christabella's side to do this by burning Alessa alive. It did not work out so well.
- Bad Dreams: Occasionally crossing into Dreaming the Truth and Dreaming of Things to Come.
- Chickification: A complaint leveled early on against the portrayal of Heather in this film compared to the Silent Hill 3 game.
- Daddy's Girl: To the point of willingly going to Silent Hill to save him, even knowing he wouldn't want her to, because that's what you do when you love someone.
- Fusion Dance: Fuses with Alessa to make them both complete.
- Helpless Good Side: Averted. She doesn't have Alessa's psychic powers or knowledge of Silent Hill, but she's no longer a helpless child and her fusion with Dark Alessa suggests that she's become the stronger half.
- Plucky Girl: Willing to go face the horrors of Silent Hill in order to rescue her father.
- Sleeves Are for Wimps: Averted. Heather wears her trademark armless jacket, but wears an orange, long-sleeved jumper under it.
- Through the Eyes of Madness: Hallucinates monsters because of her connection to Alessa.
- Trauma-Induced Amnesia: Forgot her first visit to Silent Hill completely.
- You Can Run, but You Can't Hide: On the run with Harry since the end of the first film.
Harry Mason / Christopher Da Silva
- Played by Sean Bean
- Chained to a Rock: Chained to a statue of Valtiel to be sacrificed to the Order's god.
- Disappeared Dad: Subverted. Kidnapped by the Order.
- I Choose to Stay: Harry decides to remain in Silent Hill to track down Rose.
- Ooh, Me Accent's Slipping: Sean Bean's American accent is not very convincing.
- Overprotective Dad: With good reason.
- Secret Diary: Has a journal containing all his knowledge of Silent Hill, including the Seal of Metatron.
- These Hands Have Killed: Revealed to have murdered an Order member when he attacked Heather, forcing the two to go on the run.
- Took a Level in Kindness: He cares much more for Sharon now than he did in the first movie.
- "I don't think you should go to Silent Hill."Played by Kit Harington
- Abusive Parents: Claudia raised him for the purpose of bringing them Alessa, then when he falters because Heather isn't evil like he was told, she declares him insane and sends him to be "cured".
- Adaptational Attractiveness: In the game, Vincent was intentionally designed to be "not sexy." Here, well...
- Age Lift: In the original game, Vincent Smith was in his mid-twenties. Vincent Cooper is Heather's age.
- Becoming the Mask: He was sent to "befriend" Heather to make sure she follows the Order's plan, but he soon genuinely develops feelings for her.
- Conflicting Loyalty: His mother and the teachings of the cult in which he was raised, versus his conscience and the girl he's starting to fall for. He chooses the latter.
- Dogged Nice Guy: He's quite persistent about wanting to get to know Heather, despite her insistence that she's not looking to make friends. It's because he's The Mole.
- Good Scars, Evil Scars: He has a likeness of the Halo of the Sun carved into his torso.
- In-Name-Only: The only similarity he shares with the original Vincent from Silent Hill 3 is that they have the same first name.
- The Mole: Was a plant put in Heather's school by the order to reel her in, but has a Heel–Face Turn.
- Overlord Jr.: The son of Claudia, who was raised to venture out and retrieve Heather for her destiny. He did not like this idea and became Heather's ally.
- Ooh, Me Accent's Slipping: His American accent is far from perfect.
- Ship Tease: Between him and Heather.
- Strapped to an Operating Table: Vincent is sent to Brookhaven Asylum to be ripped apart by the undead nurses by Claudia after she claims he is crazy.
- Tall, Dark and Handsome: He jokingly references it by name when trying to talk to Heather, but she points out that he isn't that tall.
- Troubled, but Cute: Vincent is a teenage Mr. Fanservice who wears a leather jacket, talks back to the teacher, and is hinted to have a difficult family. Though this trope only really comes into play when it's revealed he's Claudia's son and originally befriended Heather to get her back to Silent Hill but became conflicted about his mission.
- Waistcoat of Style: He wears one for much of the movie.
- White Sheep: Despite being Claudia's son and Leonard's grandson, he has a crisis of conscience upon realizing Heather is innocent and not evil incarnate as he was told, and confesses to her rather than continue to lead her into their trap. Compare the rest of his family's almost gleeful willingness to sacrifice her anyway.
- Played by Martin Donovan
- Death from Above: Yanked up through a grate by the Missionary.
- Death by Adaptation: In the game proper, Douglas survives the events of the game unless you get the "Possessed" ending. In addition to being Demoted to Extra, he dies here too.
- Fingore: Douglas's fingers are chopped off during the escape from the Missionary.
- Heel–Face Turn: Has one after learning who he is working for.
- Killed Off for Real: Killed by the Missionary.
- Played by Deborah Kara Unger
- The Atoner: Still feels guilty for the cruelty she brought upon Alessa.
- Ms. Exposition: Explains the details of the Order's plan to Heather.
- Wild Hair: Somebody got her a comb and her hair is covered now by a head scarf.
- "Don't be afraid."Played by Malcolm McDowell
- Affably Evil: Until he completes the Seal of Metatron and transforms into a monster.
- Cloud Cuckoolander: Condemned to the asylum by Claudia when she accused him of being corrupted by Alessa's darkness. Turns out he just knows she had been corrupted herself, knew she was the Missionary, and knew the true purpose of the Seal of Metatron.
- Good Scars, Evil Scars: He has some ugly jagged scars on his head, apparently from brain surgery intended to "cure" his visions.
- Humanoid Abomination: After putting the seal of Metatron into his chest he quickly becomes something...inhuman.
- Large Ham: Malcolm McDowell definitely hams it up.
- Living MacGuffin: Subverted. Leonard has the second half of the Seal of Metatron in his body.
- Prophet Eyes: Leonard was put away by Claudia because apparently he was able to perceive the different realities of Silent Hill. His eyes are blind as a result.
- Voluntary Shapeshifter: Leonard completes the Seal of Metatron and transforms into a monster to deliver Heather to the Cult. Heather manages to pull out the Seal and kills Leonard.
Claudia Wolf / The Missionary
- Played by Carrie-Anne Moss
- Abusive Parents: Raised Vincent to find Heather and bring her back to the town.
- Expy: Her missionary form is based heavily on three different monster designs from the Hellraiser franchise. Her black leather clothes and the way her skin has been peeled back to expose the flesh underneath is heavily reminiscent of the Angelique Cenobite from Hellraiser: Bloodline. Furthermore, the way the blades are lodged into her skull is an idea taken directly from Hellraiser III: Hell on Earth's CD-throwing Cenobite. And finally, the way her lipless mouth exposes all of her teeth is identical to the mouths of Hellraiser's Chatterer and Torso Cenobites.
- Freudian Excuse: Willing to hurt those who get in her way as long as she can complete her goal.
- Humanoid Abomination: She's actually the Missionary.
- Red Right Hand: Lacks eyebrows.
- Voluntary Shapeshifter: Really the Missionary, and the Seal of Metatron under Alessa's influence reveals this to her followers.
- Well-Intentioned Extremist: Wishes to use Heather to incubate and eventually give birth to the God of the Cult to purge the world of evil. The Cult intended to do this with Alessa years ago, but it went wrong thanks to Christabella.
Rose Da Silva
- Played by Radha Mitchell
- Heroic Sacrifice: Gave up her chance to return home by using the Seal of Metatron to send Sharon home to Christopher.
- The Man in the Mirror Talks Back: Rose appears to Chris in a mirror and explains what has become of herself.
Alessa Gillespie/Memory of Alessa/Dark Alessa
- Played by Adelaide Clemens
- Apocalypse Maiden: As seen when she uses her powers to drive Silent Hill into darkness.
- Fusion Dance: Becomes one with Heather during their confrontation.
- Playing with Fire: She sets a carousel on fire.
- Played by Heather Marks
- And I Must Scream: Presumably her fate, as she is dragged by the mannequin monster back.
Travis GradyA trucker who cameos at the end of the film and gives Heather and Vincent a ride out of Silent Hill, saying he hasn't passed through the area in years.
- Played by Roberto Campanella
- Anti-Villain: Serves as Alessa and Heather's protector and comes to the latter's aid against the crazies of the asylum, and then fights the Missionary in the finale.
- BFS: It wouldn't be Pyramid Head without the Great Knife.
- Chained to a Rock: Shown to be the operator for the amusement park's carousel, but is chained to it, implying the Order may have somehow subjugated his power until Heather summons him to help her.
- Hopeless Boss Fight: The only monster who puts up a decent fight against him is the Missionary.
- Impaled with Extreme Prejudice: His most signature attack.
- Sinister Scraping Sound: When he drags his Great Knife around.
NursesAn army of twenty-odd undead nurses, wrapped in bandages and brandishing weapons. They respond to light and movement.
- Battleaxe Nurse: Nurse monsters that attack people.
Mannequin MonsterA multi-limbed creature made of various mannequin parts. It turns people into mannequins themselves and assimilates their parts.
- And I Must Scream: The monster captures its victims and transforms them into mannequins before assimilating them into its own spider-like body.