When Drew County was created on November 26, 1846, it was a sparsely settled frontier. Its main settlement and first county seat was a hilltop village called Rough and Ready, after Zachary Taylor, which became notorious for fights, duels and lawlessness. When the county set out to build its first courthouse in 1851, it moved a mile north and founded a new town, and Rough and Ready Cemetery, now inside the city limits, is all that remains of the old village. Monticello was incorporated on December 20, 1852, and its Jeffersonian settlers named it for Thomas Jefferson's home in Virginia.
More about Monticello
A wooden courthouse of 1851 was replaced in 1857, and in March and September 1859 it saw two trials in the freedom suit of Abby Guy, an enslaved woman who said a former master had freed her but that his brother later kidnapped and re-enslaved her. The first trial ended in a hung jury, the second jury found in her favor, and the Arkansas Supreme Court upheld the verdict, freeing her and her children. During the Civil War several small skirmishes were fought around Monticello, and the Rodgers Female Academy served as a Confederate military hospital. A third courthouse, of local brick with a 110-foot clock tower, was begun on October 20, 1870, and opened in 1871.
In September 1922 a Ku Klux Klan chapter was organized in Monticello with 404 members, among them many of the town's business and political leaders, and from 1921 to 1925 the mayor, the city marshal and half the city council were Klan members.
Sources
Wikipedia: Monticello, Arkansas