As I am thinking about Taja-Nia Henderson's really exciting work on incarcertaion and slavery in pre-Civil War Virginia, the Hanover County jail comes to mind. It's right next to the Hanover County Courthouse (of recent trivia fame) and was constructed, as I understand it, in 1835. I guess that timing makes sense -- seems like that was an era of growing prosperity for the state and also the era when even better security over slaves was sought.
As of this talk of jails reminds me of the story that Scot French was the first to bring to light: the slave Boson escaped from the Sussex County jail shortly after being sentenced to execution for planning insurrection in 1831. (This was part one of the prosecutions in the wake of the Nat Turner in neighboring Southampton County.) One of the other slaves with Boson was killed in the attempt to escape -- though Boson made it out and remained free for a few years. When he was finally recaptured, tempers had cooled enough that Boson's sentence of death was commuted to transportation outside the state. There's a really interesting story about how Boson -- and in fact the other Sussex County cases -- relate to those from Southampton (and a few others, as well), which I hope to talk some about in the spring.
The illustration is of the Hanover County jail. The Spotsylvania jail is here.