The Civil War
By the time of the Civil War, Bayport had become an important port for goods being transported both in and out of the Tampa area and, although small, was a tactical stronghold when the Confederate Army needed it.
On July 7, 1864, Bayport was shelled by Union ships and the auxiliary courthouse constructed there in 1854 was burned to the ground.
Approximately 400 Union troops, consisting of one company of Union soldiers, one company of Confederate deserters, and one African-American member of the U.S. Colored Troops, marched into Bayport at the mouth of the Anclote River.
The Union troops easily overtook Bayport, confiscated horses and other supplies, and rode inland to Brooksville.
The Confederate troops in Brooksville separated into several different divisions before the Union troops reached them, but the division that remained in Brooksville scattered after being fired upon.
The Union troops confiscated more supplies, dined in the homes of Brooksville residents and then lit many of the remaining homes on fire before riding back to Bayport.
Several deserters were captured in the skirmish and were held in the Brooksville jail, including one Methodist preacher who returned to put out a fire a Union soldier had started.
Upon arrival at Bayport, the Union soldiers boarded their ships and left for Fort Meyers.
The Brooksville Raid is reenacted every year by a group or Civil War reenactors and is highly regarded as one of the best reenactments in the United States.