The old Macoupin County Jail was designed by the same architect as the controversial courthouse and the Loomis hotel.  It was built as part of the Macoupin County Courthouse project in 1867.

This medieval-inspired, Gothic Revival designed jail was in operation for 119 years - from 1869 to 1988.

This jail was built using the "cannonball" method, which prevented jailbreaks by making it virtually impossible to escape by removing the blocks. This method consisted of hallowing out the ends of each stone, then placing surplus Civil War cannonballs between the stones to lock them together. The ceilings, walls, and floors were constructed of one-inch iron plates with 20-inches of solid stone.

The jail has been closed to the public since its closing in 1988. However, in 2015 a campaign was started to fund the renovation and reopen the popular attraction to the public.