The first Civil War gunfire in Gainesville's streets came on February 15, 1864, when a raiding party of 50 men from the 40th Massachusetts Cavalry entered the city to try to capture two trains, but the raid failed when the Federal troops were met and repulsed by the Second Florida Cavalry at what is now Main Street at University Avenue. Five days later, the main Federal force was defeated at the Battle of Olustee, 50 miles to the north. Another Civil War battle was fought in Gainesville on August 17, 1864, when about 300 occupying Federal troops were attacked by Florida cavalry under Captain J.J. Dickison, called Florida's most conspicuous soldier. After a brisk fight, the Federals were driven from the city and suffered severe casualties during a hard pursuit that ended in victory for the Confederate force.
