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1950s
- July 26, 1950 - Arthur King is born.
- December 3, 1951 - Thomas Eastwood is born.
- May 14, 1953 - Jeffrey Eastwood is born.
- May 15, 1954 - Kamryn Eastwood is born.
- Unknown - Susan Eastwood is born.
1960s
- Unknown - Thomas and Arthur become best friends.
- 1969 - Isabella Eastwood is born.
1970s
- Unknown - Thomas and Kamryn become married.
- February 14, 1972 - Louis Eastwood is born.
- Unknown - Jeffrey and Susan become married.
- Unknown - Summer Eastwood is born.
- Unknown - Eastwood Games is founded by Thomas Eastwood.
1982
- April 13 - Thomas makes a recording documenting his creation of the Cinema Screen Monitor Portable Computer and his new game, Apple Acres.
- Unknown - Thomas starts to become affected by The Entity.
- Unknown - Louis makes drawings of his father acting differently.
- Unknown - Apple Acres is changed to the current title, Andy's Apple Farm.
- October 14 - Louis drowns at Lake Keystone after failing to be saved by his sister.
- Thomas and Kamryn argue over who's at fault for Louis's death. The two eventually separate.
- Arthur now looks after the family.
- Thomas and Kamryn argue over who's at fault for Louis's death. The two eventually separate.
- Unknown - Thomas and Arthur meet at the diner, discussing current events. Thomas senses an affair.
- December 22 - Thomas makes a recording documenting his discovery of his computer's ability to bring people back to life. Louis is now inside the computer.
- Unknown - Isabella continues grieving over her brother's death and her parents' separation. Kamryn reassures Isabella that it wasn't her fault.
- December 24
- The Christmas Tree in the family home's living room falls onto the nearby fireplace, starting a house fire.
- Isabella sees the fire and escapes the house.
- Kamryn is killed by the fire.
- Arthur returns from the store to see the now burnt-down home.
- Thomas goes to deliver a gift to Isabella as an apology for blaming her.
- Thomas arrives at the burnt-down home and believes Arthur was behind the fire.
- The Entity possesses Thomas to grab an axe and kill Arthur. Thomas is unable to fight back.
- Arthur is chased by Thomas through the woods before being axed to death.
- A hiding Isabella sees Thomas kill Arthur.
- Thomas realizes what he has done and drags Arthur's corpse to his computer to bring him back to life.
- Isabella waves down a family in a car for help.
- The Christmas Tree in the family home's living room falls onto the nearby fireplace, starting a house fire.
1983
- Unknown - Isabella is questioned by the police to tell what happened on Christmas Eve.
- March 17 - Thomas is killed after attempting to confront The Entity.
- Unknown - Jeffrey takes Isabella in.
- Unknown - Thomas finds himself reborn in Andy's Apple Farm along with his friends and family but have now taken on the form of the game's various characters.
1986
- Unknown - A Halloween Episode for Andy's Apple Farm is created by Jeffery to promote the game.
- Unknown - Rabbit Knight is the last game created by Eastwood Games.
- August 22 - Jeffrey is killed.
- Isabella later discovers Jeffrey's corpse in the living room.
- October 30 - Jefferey as the Rabbit Knight tries to save Isabella from the Entity but he ultimately fails, and as punishment is banished to Andy's Apple Farm along with the other souls they have collected.
2021
- August 17 - Logan Eastwood creates a YouTube account. He does a playthrough of Andy's Apple Farm.
- August 26 - Logan continues the second half of his playthrough.
