The Middle Florida cotton plantation region that centered in Tallahassee had good reason in the spring of 1864 to fear an attack by Federal forces despite the impressive Confederate victory at the Battle of Olustee on February 20. After this bloody engagement Union troops retreated to Jacksonville, and pursuing Confederates stopped twelve miles short of the city at McGirt's Creek. They dug in there, and for months there was a standoff. Florida’s long and poorly defended shoreline provided abundant other opportunities for a Federal assault, however. Middle Florida had become particularly vulnerable to an attack with the withdrawal of Confederate forces to meet the Federal threat at Olustee. A band of deserters hidden in the swamps of Taylor and Lafayette counties had been raiding the plantation country and had become so destructive that in March 1864, a force was sent to try to clear these renegades out of the swamps. These dissidents had also occasionally assisted landing parties from Federal gunboats in raids on salt works. One such raid was near St. Marks, within thirty miles of Tallahassee, on the three days preceding the Battle of Olustee, and $3,000,000 worth of property was destroyed.
"How to Escape the Yankees: Major Scott's Letter to his Wife at Tallahassee, March 1864,"
Florida Historical Quarterly: Vol. 50
, Article 7.
Available at: https://stars.library.ucf.edu/fhq/vol50/iss1/7