Madison County, established in 1846, was named for James Madison, the fourth president of the United States.  The county originated in 1849.

Madison's first courthouse was a one-story log cabin built in Winterset in 1857. The second courthouse was built in 1868-69 completely with Madison County gray limestone, but was destroyed by fire in 1875.

The current Madison County courthouse was built by Andrew Piquenard, planner of both the Iowa and Illinois State Capitols. It was entered in the National Register of Historic Places in 1966.

In 1969, the courthouse and surrounding square were the setting of the movie "Cold Turkey" starring Dick Van Dyke.

President Ronald Reagan visited the courthouse in 1984.