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Drew County was established in 1846 by its citizens. They decided to build a new county seat. The land for the new town was donated in 1849. In 1851, the first courthouse was constructed. A second one was built in 1857.
In that courthouse, two trials were held in March 1859 and September 1859 to determine whether Abby Guy should be freed. She claimed that her former master had evicted her, but that she was kidnapped illegally and re-enslaved years later by her brother. Her first trial in her freedom case ended in a hung jury, but her second trial was decided by twelve local white men. She was assisted by top lawyers and married another white man. Guy won the appeal to the state Supreme Court. Her children and she were freed. Her children and she were set free because she was a free woman.
A few small skirmishes took place around Monticello during the Civil War. Confederate soldiers were treated at Rodger's Female Academy.