At the age of 25, Harry and Jodie found a baby on the side of a road, whom they took home and named Cheryl. However, three years later, at the age of 28, Harry's wife acquired a fatal disease and suddenly died. For the next four years, Harry raised Cheryl alone.
At 32 years old, Harry was still in deep grief over his wife's death. Cheryl, who was now seven, convinced Harry to take a peaceful vacation to relax in the resort town of Silent Hill. Harry agreed, but as they prepared for the vacation, they entered the town late at night due to engine problems. While Harry was driving towards the town with Cheryl in the front seat, he saw a young woman, who is later revealed to be Alessa Gillespie, walk into the path of his vehicle. He tried to avoid her, but lost control of the vehicle and fell off the side of the hillside trail. He later awoke in the town to find Cheryl had gone missing.
In Silent Hill, Harry meets many people. He forms a bond with Cybil Bennett, a police officer, and they attempt to find his daughter. However, Cybil doesn't seem to understand Harry when he talks about phenomenal things, such as his dreams of the Otherworld and reality. Dahlia Gillespie, a priestess of a cult named "the Order", often gives clues to help Harry, yet also confuses him in doing so. While exploring the town, Harry often encounters Dahlia's daughter Alessa, although she always disappears before Harry is able to speak to her.
In Alchemilla Hospital, Harry meets a doctor named Michael Kaufmann and a young nurse, Lisa Garland, who grows attached to Harry after he meets her. They have conversations about Silent Hill's past and Harry offers to take her with him, but she declines, stating that she doesn't feel she should leave the hospital.
Harry, Cybil, and Dahlia meet up in the Resort Area to stop Alessa's plan to unleash hell on the town. In order to do this, they need to use the Flauros to stop Alessa before she places the "Mark of Samael" on the lighthouse and Lakeside Amusement Park. Harry arrives at the lighthouse too late, so he heads over to the amusement park to regroup with Cybil, who has been infected by a parasite. Harry has no choice but to defeat her in battle, and Cybil is ultimately killed. Dahlia reveals to Harry that the Mark of Samael is actually a sigil that repels against the cult's god, and Harry realizes he has been deceived.
Harry is then transported to Nowhere, where he reunites with Lisa. Lisa transforms into a deranged nurse, and Harry retreats against a wall in fear as she approaches him, yearning for solace. He locks her in a room alone as she cries, though he feels sympathy for her. With Cheryl and Alessa restored to one being, Dahlia attempts to birth God again during the final showdown. However, Michael Kaufmann arrives with Aglaophotis and uses it on Alessa, expelling a monster known as the Incubus from her, which kills Dahlia using lightning. Harry defeats the Incubus in battle.
As the Otherworld crumbles in flames after the monster's defeat, Lisa reappears for a brief moment and kills Kaufmann before he is able to escape, successfully taking her revenge on him. The Incubator (Alessa) gives Harry a baby, a reincarnation of both Cheryl and Alessa, and opens a portal for him to escape. Harry enters the portal and is seen leaving Silent Hill with the newborn baby in his arms. He safely makes it to the highway on the outskirts of the town and stares up at the sky, bewildered at everything that has happened.
Portland and murder caseEdit
After the first game, Harry lived an ordinary life in Portland with his new, adopted daughter. The religious organization of Silent Hill, the Order, had planned to abduct the reincarnated Cheryl/Alessa and proceeded to track her down.
Five years after the events of the first game, in 1988, Harry killed a cult member who attempted to kidnap the reincarnated Cheryl/Alessa with a gun in self-defense. Harry was acquitted in court and relocated to another town to hide incognito.
To ensure his adopted daughter's safety, he dyed her hair from brunette to blonde and named her Heather. Afterwards, he eventually settled in the Daisy Villa Apartments with her. Despite feeling confused and frustrated at who Heather could be, Harry was determined to raise her.
Silent Hill 3Edit
After Harry raised Heather in the unnamed town for 12 years, the events of Silent Hill 3 take place. Because the game takes place 17 years after the events of the original Silent Hill, Harry is now 49.
The story of Silent Hill 3 is a continuation of that of the first game. The latter half of the game reveals that Heather is actually Cheryl/Alessa reborn, and that her father was Harry Mason. In this installment, Heather runs an errand for her father at the mall and phones her father telling him that she is coming home. Heather's last words to Harry in their conversation are "I love you too, Dad."
When she returns home, Heather discovers her father slumped in a chair, having been brutally murdered by the Missionary under Claudia Wolf's orders. Heather gasps at the sight and sobs uncontrollably, saddened by the sudden loss.
After defeating the Missionary by herself, Douglas Cartland helps Heather move her father's body into his bedroom and covers him with a sheet and lilies. Heather decides to kill Claudia in revenge for her father's death, who is waiting in Silent Hill. Before their car ride to Silent Hill, Douglas gives Heather a postmortem notebook from Harry. The notebook details Harry's experiences from the first Silent Hill game and is a final goodbye to his daughter. Heather wonders if her father would be mad at her decision if he were still alive and promises to return home.
In the chapel, Heather encounters a facsimile of her father's bedroom while traversing the Otherworld church. There, Harry's corpse is missing from the bed, which is stripped of its coverings with scattered lilies on the floor, and a trail of blood leads to the door. If Heather examines the bed, she will state, "This room looks just like Dad's. It's more than just a resemblance. Dad's not sleeping in the bed, though."
After defeating God, Heather mourns over her father's death one last time. Just as she is ready to leave, Heather looks behind her at what is unseen by the player, which may have been Harry's presence.
At the end of the game, when Douglas calls Heather by her name, Heather states that she isn't hiding anymore and wants to be called Cheryl, the name her father originally gave her. The game closes on an image of Heather putting flowers next to Harry's grave, having given her father the burial she wanted him to have.
In Silent Hill 3's UFO ending, Heather returns home to find that Harry is not dead and tells him about her hardships. Infuriated, Harry obliterates the town of Silent Hill with the help of aliens.