The Overlook Penitentiary is a location in Silent Hill: Homecoming and Silent Hill: Downpour. The penitentiary's whereabouts seem to differ greatly between the two games: in Homecoming, it is located in Central Silent Hill; in Downpour, it is located on an island in Toluca Lake, near Southeastern Silent Hill. The building is not seen or mentioned in any previous games.
Built as a two-story prison, Overlook contains two wings for inmate populations. Cell Wing A consists of cells A1-A20, with A1-A4 and A10-A14 located on the first floor, and A5-A8 and A15-A20 on the second. Cell Wing B follows an identical pattern. Two guard rooms are located upstairs, flanking each cell wing, while only one guard room is apparent on the first floor. Also on the first floor is a shower area connecting the two cell wings and solitary confinement, which is inaccessible until power is restored to its lock, located just off of Cell Wing A. As demonstrated by Wheeler in his attempts at helping Alex Shepherd, the penitentiary seems to be wired with many cameras. This is apparent as Wheeler, stationed in a guard room, is aware of Alex's location at all times.
The prison appears to have been abandoned for years and is in a state of intense disrepair, much like the rest of Silent Hill and Shepherd's Glen. From information found in a prisoner's note, it is implied the staff all disappeared suddenly, leaving the prisoners to die. The Order appears to have taken up use of the facility, possibly using it as a temporary squat for their prisoners. How long they have claimed domain of the structure is unknown.
Silent Hill: Homecoming
After Alex Shepherd, Elle Holloway, and Wheeler arrive in Silent Hill, the latter two are captured by the Order and taken to Overlook. After finding a way inside, Alex finds Wheeler, and the pair fight their way to Solitary Confinement where Wheeler overheard a woman was being kept. Alex can only enter after he disables the electric fence by shutting off the power at Toluca Lake Water and Power.
Like many areas of Silent Hill, the Otherworld's influence corrupts the penitentiary, albeit briefly. While its location in relation to its Fog World counterpart is not made clear, some sections seem to correspond to other areas in the Fog World. This is most notable in that the final chamber of the prison, which may be a type of execution chamber, is unexplored in the Fog World.
The transformation to the Otherworld occurs immediately after reaching Solitary Confinement, with Alex's new goal at this point being to escape. Upon reaching the final area of the prison, Wheeler and Alex find Margaret Holloway bound to a chair. As the pair attempts to rescue her, Wheeler is abducted by the monster Asphyxia. Alex frees Holloway, who flees and locks Alex in with an evil grin. Moments later, Asphyxia returns and Alex is left to fight her alone.
Silent Hill: Downpour
A completely re-imagined version of Overlook Penitentiary serves as the final area of Murphy Pendleton's journey in Silent Hill. The prison now resembles Ryall State Prison rather than the two-story building in Homecoming. After being shot by Anne Cunningham, Murphy wakes up in a cell at Overlook, donned in a prison uniform. While the change of location cannot be easily explained, the differing interior may be due to the differing nature of Alex and Murphy's psyche, the town changing the prison to better fit Murphy.
At the end of the area, Murphy fights the Wheelman, has his past revealed, and has his fate decided.
- Overlook Penitentiary was most likely named after the Overlook Hotel, the setting of the story The Shining.
- There is graffiti in most of the cells, one specific piece of which reads "Watson Lives". This is most likely a reference to John Watson, one of the script designers.
- In Homecoming, many cells have statements written on the walls, however appear to be done in charcoal rather than spraypaint. These statements include quizzical and even self-analyzing pieces such as: "Somewhere down there is your soul", "My cell has something from everyone else's cell", "Hell here", "Capt. Coatrack shall return", "Nothing is real", "Jafo is watching you", and countless others. Occasionally the player can even locate ones of humor, such as "I like pizza" or "I am the walrus" (a reference to a Beatles' song).
- In Silent Hill: Homecoming, Lady Justice can be seen on its sign.
- There is speculation that the execution chamber at the end (in Homecoming) is a gas chamber. Margaret Holloway's intended execution site may be seen as karmic, based on how she murdered her daughter.
- According to Tomm Hulett, the prison in Homecoming is not the real Overlook, whereas the prison in Downpour is. Its placement in Central Silent Hill is simply a result of the powers of the town.
- In Downpour, the riot Murphy hallucinates of while crossing a balance area is likely a vision of the "distraction" George Sewell had mentioned while Murphy was supposed to kill Frank Coleridge in the washrooms.