History of Events Commemorated by the Brooksville Raid

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History of Events Commemorated by the Brooksville Raid

It was the summer of 1864. Sources state that four ships numbering 240 men from the 2nd Florida Cavalry (Union) and the 2nd U. S. Colored Infantry unloaded near Bayport. Many of the Union soldiers were familiar with the terrain, as twenty percent of the men from the 2nd Florida Cavalry were Hernando County natives.

Their visit was short but not with not without a purpose. Their intention was to crush the export industry that was aiding the Confederate Army. The exports coming from local plantations were shipping from Bayport. By cutting the supplies of cotton, cattle, and other goods shipped from the port they hoped to cripple the thriving Confederate Army and bolster their own efforts in the Civil War.

Their plan was simple, steal supplies to prevent their shipment out of Bayport and across the Gulf of Mexico to the Confederate Army. Plantations in and around Brooksville owned by David Hope, William B Hooker, Thomas Ellis, Leroy G Lesley, and Aaron T Frierson were targeted. With a minimal amount of Confederate soldiers, local protection of the community was left to volunteers, who stepped up and bravely fought back against the Union Army the best they could. All of them filled with a passion to protect their homes and their livelihood.

The Raid was extremely small in comparison to other large, and elaborate battles that were fought elsewhere during the Civil War. In actuality it was just a skirmish. Mostly with Confederate soldiers and the volunteers firing at the passing Union soldiers from behind trees and bushes, as they marched through the marshland creating turmoil and upset. It was an effort on the part of the volunteers to try to stop or at least minimize the damage to be done by the Union soldiers. As the Union soldiers made their way across the county they not only stole what supplies they could but set fire to many barns, crops and homes.

Confederate soldiers and volunteers were outnumbered 3 to 1 but did their best to stop the Union Army. Shots were fired and while there were casualties on both sides, they were minimal. To the Union Army this raid was minor if not forgotten in their history of the Civil War but here locally it will forever be remembered. Even though the Union Army won, they did not win without a fight; making their stealing and burning a bit more difficult if nothing else. I’m sure the Union Army got a little more resistance than they had expected.

On Jan. 21 & 22, 2017, the 37th Brooksville Raid Reenactment will commence at the Sandhill Scout Reservation. For additional information go to: http://brooksvilleraidreenactment.com/

*Editor's Note: Some sources say that the soldiers headed north along the path of the Anclote River toward Confederate-held Brooksville, but the geography doesn't seem to work out if they disembarked at Bayport.