According to official island legends Anna Hobbs was completely insane, she murdered her family in the Whitten Mansion where they lived together.
She overheard her mother and Reginald Whitten discussing sending her to a mental institution. This caused her to snap, and she stripped naked and wore a bag over her face with two holes in it so she could see, also armed with garden shears. She started off her murders by killing her mother, stabbing her four times in the chest with the garden shears. After, she killed her brother by slicing his head open with the garden shears. She went to the Whitten house, and murdered Reginald Whitten the same way she did her mother. Mrs. Whitten watched on in horror.
Overwhelmed by the horrific thing she had done, she went to the lake removed the mask and decapitated herself with the garden shears she used to murder her family. Her headless corpse and severed head fell into the lake.
Near the end of the Halloween special, Noah and the Lakewood 5, excluding Emma, found a secret passage from the Whitten house to the Hobb's house. Noah theorized upon learning the location the passage goes that Whitten was having an affair with Anna's mother. But when Whitten turned his eyes on Anna, her mother attempted to protect her daughter. But Whitten, accustomed to getting what he wants, murders the mother out anger. Then he killed Anna's little brother by slashing his chest for witnessing the murder. Whitten stabbed Anna in the stomahc with the garden shears, but Anna was able to stab him back slicing his chest open. Anna went to the dock in order to get help, but succumbed to her injuries. According to Noah, Whitten's wife found his body and moved it to their bed to make it appear that Anna had killed her family then killed her husband.