The first jail was a log cabin built in 1832 in Washington Township. Plans were started for a new jail in 1836. It was to be 36 by 27 feet and made of brick. The criminal room was to be built with nine-inch square oak timber inside the brick wall.

By 1841, the building was completed enough to be declared unsafe and it was ordered that the building be lined with two-inch oak plank and iron bars over the windows and doors. In 1863 another jail was built at a cost of $12,000.

Fifteen years later, in 1878, a new jail was built at 123 West Washington Street in Greencastle. A second jail was built at that same location in 1939, and it was used until 1995.