According to the United States Census Bureau, the city has a total area of 6.1 square miles (16 km2), all land.

[9] Joshua Jones, a surveyor and Revolutionary War veteran, laid out the town on 13 acres owned by William Beard.

[16] The first recorded school in Wayne County was opened around 1800 by Robert Ferrill, a well-educated wheelwright who had a few good books.

Monticello's first school was opened in 1807 by Rodes Garth, who taught "Roman history, the Scriptures, orthography, and pronunciation."

In 1819, Yale graduate John S. Frisbie began a school with Michael Huffaker as the first teacher of record.

The Monticello Academy was established in 1830 with John Lankford as the headmaster, followed by Professor Mullins, and later William Burton.

In 1843, under the guidance of Commissioners Micajah Phillips, John Rousseau, Martin Beaty, and Francis Goddard, the county voted and ratified to organize into common school districts.

The first examiners for receiving a teaching certificate were physician Jonathan S. Frisbie, lawyer John Lankford, and teacher Littleton Beard.

Teachers at these schools before the Civil War include Amanda McGee, William and Thomas Simpson, Joseph Ballou, and Marcellus Baugh.

The first school superintendent of Wayne County was Robert McBeath, a "member of a family noted for their intellectual qualities."

Ones in the 1880s and '90s include Lucy and Amanda Taylor, Sallie and Eula Kendrick, Emma Kelley, Fount Cooper, William Sandusky, Tobias Huffaker, and Mollie Denny, who became the Wayne County superintendent.

Programs include health science, welding, carpentry, machine tooling, automotive repair, 3D printing iechnology, industrial maintenance, and business.

Max Wise of Campbellsville is the current Kentucky state senator, representing District 16, which includes Wayne, Adair, Clinton, Cumberland, McCreary, Russell, and Taylor Counties.