Established in 1827, the Old City Cemetery is the oldest of Monticello's cemeteries, while the adjacent Roseland cemetery was established about 1850.

These cemeteries contain the remains of local Confederate soldiers and officials, as well as some soldiers who were brought to Monticello and died there after being wounded at the Battle of Olustee. Among the Confederate veterans buried here is William S. Dilworth, a prominent Monticello attorney who was a delegate to the Florida Secession Convention and served as a colonel in the 3rd Florida Infantry.

At one point early in the war, Colonel Dilworth commanded all troops in the Military District of East and Middle Florida. In May 1862, Colonel Dilworth and his unit were transferred out of

Florida and the regiment served in the western theater until the end of the war, although Dilworth himself returned to Monticello in July 1864 on extended sick leave.

Another Confederate veteran buried here is Samuel Pasco, who served in the 3rd Florida Infantry and was captured at the

1863 Battleof Missionary Ridge in Tennessee. He spent the remainder of the war in a Union prison camp in Indiana before

being paroled in 1865 as a sergeant. In the postwar period, Pasco was a state legislator and United States Senator; Pasco County, Florida was named in his honor in 1887.

Also buried here is Smith Simkins, a lawyer and the first sheriff of JeffersonCounty, who manufactured salt for the Confederacy at various points along the county's Gulf Coast. Simkins was also one of the four members of the Florida Executive Council which met in 1862 to develop the state's war policies.

Information Provided by the Florida Department of State.