The Holloway Family is one of the four founding families of Shepherd's Glen. They were given the duty of Keeper of Lore and were to sacrifice their children to the noose, shown to mean general suffocation. This must be done to maintain the pact held with the Order and their god. Their place in the contract also puts their family in charge of the judicial duties of Shepherd's Glen and places them in charge of the Town Hall.
The Holloways' emblem depicts a bird resting on a law scale. The law scale would relate to Margaret Holloway's position as a judge.
- Edwin Holloway (1820 - 1879)
- Edith Holloway (???? - ????)
- Ann Holloway (???? - 1853)
- Frederick Holloway (1865 - 1900)
- John Holloway (1868 - 1901)
- Nancy Holloway (1870 - 1899)
- Henry Holloway (1885 - 1892)
- Earnest Holloway (???? - 1903)
- Robert Holloway (1887 - 1910)
- Sophie Holloway (married into family, wife of John) (1889 - 1920)
- Karen Holloway (daughter of John and Sophie) (???? - ????+8)
- Lawrence Holloway (???? - 1953)
- Margaret Holloway (1954 - 2007)
- Elle Holloway (daughter of Margaret) (b. 1985)
- Nora Holloway (daughter of Margaret) (1992 - 2003)
- In the Centennial Building in Silent Hill: Downpour, a Professor Horace Holloway is mentioned as an early settler in the Toluca Lake area in a particular book.