As the self-proclaimed Caretaker expert: As far as I know Cindy was an orphan in Carey Ohio and got taken in by the Good Harvest Orphanage where the adults were neglectful of the children...because of course they were. One Halloween, Cindy, who for whatever reason has telekinetic powers, set fire to the Orphanage killing everyone inside and used the fire as a chance to escape. Somewhere along the way she gets adopted by the Caretaker, who was as the name implies, the Caretaker of the Shady Oaks Cemetery in Carey Ohio. (Though if you find press material from 2002 it claims he lives with his family in Williamette Georgia, because this was before A&D decided to center most of their original lore in Carey Ohio.) Cindy lived with the Caretaker and his family up until the townspeople figured out that he was using the bodies of their deceased loved ones in the cemetery for his experiments and research into the human soul and how to resurrect the dead. In an act of vengeance they burned his house to the ground. While the Caretaker was able to escape, Cindy perished in this fire and as a result the Caretaker redoubled his research into brining the dead back to life with the express purpose of using it to bring Cindy back to life. Somehow, someway he has succeeded as that's how she's able to pop up at the event as a living scareactor every now and then, and not as a mannequin like she was in 2006.