Silent Hill Edit
In the original Silent Hill, Harry travels to Silent Hill for vacation with his adopted daughter Cheryl. Driving towards Silent Hill, he sees a young woman in the middle of the road which he serves to avoid. He crashes his red Jeep and awakes to find his daughter missing.
While exploring the town of Silent Hill, he meets many people and monsters. One of the people he meets is Cybil Bennett, a police officer from Brahms, and they both attempt to find Harry's daughter. However, Cybil doesn't seem to understand the phenomenal things, such as the Otherworld. Dahlia Gillespie, a priestess of the cult called The Order, often gives Harry clues and hints to help him, but yet confuses him. Harry also meets the director of medical staff at the hospital, Doctor Kaufmann, and a young nurse named Lisa Garland. Harry often talks with her, learning about the history of the town.
At the end of the game, in Nowhere, Harry faces off against the Incubator/Incubus. After the fight, the Incubator gives Harry a new baby, who eventually becomes Heather Mason. During the end of the game, Harry escapes Silent Hill with his new baby and Cybil (depending on the ending).
Silent Hill 3 Edit
Before the events of Silent Hill 3, Harry moves to Portland and lives an ordinary life with his new adopted daughter, Heather. The Order planned to kidnap Alessa/Cheryl (Heather) and five years after the first game, Harry killed a cult member attempting to kidnap Heather. They move to an unnamed town and dyed Heather's hair from black to blonde in order to protect her. Afterwards, they finally settle in at Daisy Villa Apartments in another unnamed town.
During the events of Silent Hill 3, Harry had been raising Heather in their current unnamed town for 12 years. At the beginning of the game, Heather is chatting with her father from a pay phone at the mall. She ends the conversation with the words "I love you too, Dad".
Later when Heather escapes the nightmarish Mall, Subway, Sewers, and office building areas, she finally arrives home. But to her dismay, she finds her father murdered. She soon discovers on the roof that the Missionary brutally killed her father under Claudia Wolf's orders.
Silent Hill: Shattered Memories Edit
In the re-imagining of the original game, Harry Mason's role and personality is changed. However, his main objective of finding his missing daughter, Cheryl, hasn't been changed very much. At the end of the game, Harry is revealed to be nothing more than a physical manifestation created by Cheryl from her memories. The real Harry Mason actually died over decade prior to events of Shattered Memories.
Other appearances Edit
Silent Hill 2: Restless Dreams Edit
In the UFO ending of Silent Hill 2: Restless Dreams, Harry descends down from a spaceship asking James Sunderland if he had seen his daughter while James in turn asks if Harry had seen Mary. James is zapped by a ray gun and dragged onto the ship.
Silent Hill: Origins Edit
In the ending of Origins, Harry's voice can be heard discovering Cheryl in a field with his wife.