Constructed in 1906, this building replaced a stone jail that had been built 100 years earlier. That structure featured a jail yard, wooden fence, and small, dark cells that were called the “dungeon.”
This new jail was designed to improve prisoner’s living conditions and the appearance of the area. Cells were located in the rear portion, which was designed to be formidable to deter potential criminals and escapees. However only a few people would be housed in the jail at one time since only those awaiting trial or serving very short sentenced were incarcerated here. Anyone else would be sent to one of the state’s numerous road camps or prisons.
The front portion was more welcoming. It housed the Sheriff’s office on the first floor and a second floor apartment for him and his family. These residential quarters were placed here so the Sheriff, his wife, and children could also serve as around-the-clock jailer, cook, and janitor.
A new cast-iron fence was also constructed at the time to surround the jail yard. This would become a popular place for Woodstock residents who, during their visits downtown, regularly socialized with each other while leaning on the fence.
Between 1916 and 1933 Virginia experiment with statewide prohibition of alcohol and the jail saw one of its busiest periods. In his publication “Prohibition is Wrong” local lawyer Gilbert Pence observed on average approximately 700 individuals were incarnated for some point in time at this jail each year during that period.
The county Sheriff and his Deputies were kept busy tracking down individuals accused of violating these prohibition laws and destroying illicit alcohol. On June 14, 1925 the Woodstock Times and Edinburg Sentinel reported on one such occasion when the Sheriff destroyed over 60 gallons of whiskey under the watchful eyes of court officials.
Even though Prohibition’s end reduced the number of criminals in the county, by the 1960s the jail was seriously overcrowded and outdated. The convict population had soared as the local population increased and the state expected local jails to house more prisoners. Deputies also now staffed the jail 24-hours a day and served as emergency dispatchers. There were also no separate facilities for male and female prisoners. So in 1974 this structure was demolished and a new jail, attached to the newly completed Circuit Courthouse, was constructed.