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The Battle of Olustee, held near Lake City, was the largest battle in Florida throughout the Civil War.
Fought on February 20, 1864, the Battle of Olustee (also known as the Battle of Ocean Pond) was the largest Civil War engagement in Florida. Political and military considerations both played a role in the campaign’s origins. Republican leaders hoped to see a loyal Florida government returned to the Union under the terms of President Lincoln's 1863 Reconstruction Proclamation, and to send delegates to the 1864 Republican presidential convention.
Major General Quincy Gillmore, commanding the Union Army's Department of the South, hoped to prevent the flow of supplies to the Confederate armies and obtain recruits for the Union army's black regiments. About 6,000 troops were selected for the operation, with Brigadier General Truman Seymour in direct command. They occupied Jacksonville on February 7, and over the next several days, mounted raids into the interior.
The Olustee defeat ended Union efforts to organize a loyal Florida government in time for the 1864 election, though they did maintain their presence around Jacksonville.
The Confederate commander of the District of East Florida was Brigadier General Joseph Finegan, with only about 1,500 troops. He called for reinforcements, which eventually brought the number of defenders to more than 5,000, and built a strong defensive position east of Lake City at Olustee.
While the Confederates prepared, the Federal commanders bickered over their next movement. Seymour was pessimistic, believing that an advance on Lake City was not possible and that Unionist sentiment in Florida was less than the Federals had been led to believe. Gillmore ordered that defensive works be constructed and that no advance be made westward without his consent. He then left Florida, returning to his headquarters in South Carolina. Seymour's confidence soon returned; he wrote that he now intended to advance to the Suwannee River to destroy a railroad bridge there. Gillmore dispatched an officer to stop the movement, but the Battle of Olustee occurred before he arrived.
Early on February 20, Seymour's army left Barbers Station for Lake City. When Finegan learned of the enemy's approach, he ordered his cavalry to draw the Federals towards his defenses. The fighting to the east intensified, however, and Finegan sent out additional troops to assist those already deployed.
By mid-afternoon the skirmishing had escalated into a major battle. While Union Colonel Joseph Hawley positioned his brigade, a wrong command was given and one unit fell into confusion and quickly fell apart. This directed Southern attention towards an untried black regiment, which occupied the Union left. It held the line for a time, suffering more than 300 casualties before retreating. With the destruction of Hawley's Brigade, Brigadier General Alfred Colquitt, in direct command of the Confederate attack, ordered a general advance. Seymour deployed another brigade to stop it, which stabilized the lines for a time.
The fighting during this phase of the battle was particularly severe. The Confederates captured several Union artillery pieces and threatened to flank the Federal infantry. By late afternoon, Seymour realized the battle was lost and sent forward his last reserves, the 35th U.S. Colored Infantry and the 54th Massachusetts, to protect a withdrawal. Many wounded and a large amount of equipment had to be abandoned. In the battle's aftermath, bands of Southern troops killed or mistreated some of the black Union soldiers left on the field. Fortunately for the Federals, the Confederate pursuit was poorly conducted, enabling most of their force to escape. The Federals suffered 1,861 killed, wounded and missing in the battle, while rebel casualties numbered 946. The Olustee defeat ended Union efforts to organize a loyal Florida government in time for the 1864 election, though they did maintain their presence around Jacksonville for the remainder of the war.
To learn more, see: Confederate Florida: The Road to Olustee by William H. Nulty, University of Alabama Press, 1990
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