Macoupin County Jail

This building in Carlinville, Illinois looks like a tiny medieval fortress. It’s actually the old county jail.

The Macoupin County Jail opened in 1869 and was an early work by architect E.E. Myers, who would go on to become the only architect to design three state capitol buildings. He built the jail alongside his other Carlinville project - the so-called “Million Dollar Courthouse,” which was commissioned to be impressive enough to put Carlinville in the running for state capitol of Illinois. While the courthouse was built in a Neoclassical tradition, for the jailhouse, Myers opted for a particularly amped-up version of Gothic Revival. It may just as well have a moat and drawbridge. 

The structure’s interior is built in a style known as “jailer residence,” which includes an apartment for the jailer and his family above the cell block. In order to prevent jail breaks, leftover Civil War cannonballs were cemented into the stone walls, making the blocks nearly impossible to remove. In its 119 years of operation, only one prisoner escaped. He was soon apprehended a few blocks away. The version of that story that has entered local legend has the man wriggling out one of the narrow slit windows, grabbing a drink down the street, and returning of his own free will through the front door.

The jail was finally retired upon construction of a new county jail in 1988.