Defeat Her.

Reach Room 312.

Spend 10 minutes out on Toluca Lake.

Find His room.

Kill at least one enemy with Wooden Plank, Steel Pipe, Handgun, Shotgun and Rifle in a single playthrough.

Kill 75 enemies with melee weapons.

Reach the end of the long staircase.

Defeat the Flesh Lip.

Meet Maria.

Enter the Otherworld for the first time.

Reach Wood Side Apartments.

Try to leave Silent Hill in the Observation Deck area.

Each ordeal paves your path to what you are meant to be.