Road Trips & Scenic Drives

Old Macoupin County Jail


This historic jail has leftover Civil War cannonballs embedded into the stones used to build the walls.

The historic jail was in service from 1869 to 1988. This Gothic Revival stone structure was built using the "cannonball method." Stones were hollowed out and leftover Civil War cannonballs were embedded into the stones used to build the walls, making an escape by removing stones nearly impossible. The jail was built to hold 17 prisoners, but at sometimes, it was reported to house twice that number. Today, it is a popular tourist attraction, though admittance to the interior is no longer allowed due to structural issues.

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