Monticello was laid out in 1834 as the county seat,[8] with a post office established that year, and is still currently in operation.

[9] The city was named after President Thomas Jefferson's estate in Virginia.

[10] Monticello, Indiana sustained serious damage by a tornado on April 3, 1974, part of the 1974 Super Outbreak that caused death and destruction across the midwest and south.

[11] The aftermath of this storm is recorded in the Herald Journal's book, Killer Tornado.

[11] In the immediate aftermath of the storm, news outlets reported three hundred deaths across the United States and the creation of temporary morgues.

[12] The local paper said the aftermath was similar to a World War II bombing.

The company manufactured outdoor furniture such as folding chairs, umbrellas, and seat cushions.

Due to the materials used in making these products, four city blocks were contaminated with toxins.

The Monticello Carnegie Library, James Culbertson Reynolds House, and South Grade School Building are listed on the National Register of Historic Places.

Woodlawn Elementary School was previously part of the district until it was closed in 2013.

Students resumed classes in local churches and then in portable units erected near the location of the high school until reconstruction could be completed.