The Brooksville Raid- June 30-July 13, 1864

The Union military outpost at Fort Myers commanded by Captain Jonathan Childs was responsible for disrupting inland Confederate supply lines along the Gulf coast that were inaccessible to the Navy. Early in July of 1864 they would invade Hernando County. On June 30th two companies of the 2nd FL Cavalry (unmounted) and two companies of the 2nd United States Colored Troops (USCT) would march 10 miles in the rain to the Caloosahatchee River. Many members of the 2nd FL Cavalry were Unionists from Hernando County. They would be fighting neighbors who had forced them off their lands. Acting Master James Russell commander of the Ariel would be responsible for transporting the 260 men by sea. He would be helped by the Stonewall, Sea Bird and Rosalie. The ships got underway at 8:00 AM on July 2nd. They only made 25 miles the first day to Charlotte. They got underway again on the 5th. On the 7th they were just off Anclote Key. They landed on the north side of the Anclote River later that day. After the men were unloaded the Sea Bird, Rosalie and Stonewall returned to Tampa while the Ariel headed north to Bayport where the men were to be picked up on the 12th.

Captain Childs (illness) and 8 men who could not march were left on the ship. This would leave Captain John Bartholf in charge of the expedition. After a short march they went into camp around 8:00 PM. They were back on the march at 3:00 AM on the 8th and just after sunrise encountered an 18-man picket post. The post was part of a local home guard commanded by Captain Leroy Lesley, a local preacher and rancher. Lesley would command only about 60 men. One Federal was wounded and seven Confederates and nine horses captured. Around noon they would capture three more Confederates and their horses. They advanced another three miles when Captain Daniel’s became ill, and they decided to camp for the evening. On the 9th after about three miles, they ran into more pickets one of whom escaped to Brooksville to warn Confederates there and request reinforcements from Tampa. As the Federals advanced they encountered a group of Confederates on the opposite side of a creek. Skirmishers were thrown out and a party of 30 men sent to flank the Confederate left. The remainder of the 2nd FL Cavalry advanced with the USCT in reserve. After a brief firefight the Rebels fled.

They marched on after a short stop for breakfast at a local farmhouse meeting resistance along the way. They went into camp that evening at the plantation of David Hope. They looted and burned Hope’s home. On the morning of the 10th they stopped at the Ellis farm (Captain Thomas Benton Ellis). After looting the farm they set fire to the Ellis home but a member of the 2nd FL Cavalry returned to put the fire out. Around noon, one to two miles outside Brooksville, after being told that the town was abandoned, Captain Bartholf decided to turn off the road and head west towards Bayport about 18 miles away. Later day they looted the William Hooker farm, burned and looted Aaron Frierson’s farm and home, and burned and looted the farm but not the home of Leroy Lesley (the local home guard Captain). They continued west toward the Chassahowitzka Swamp camping 2 miles outside Bayport.

Acting Master James Russell had arrived at Bayport with the Ariel and Sea Bird on the 10th. He sent Acting Ensign Bacon into town under a flag of truce. There were only five or six families of women and children there and 11 bales of cotton on the wharf. There were another 20-30 bales in a schoolhouse. Four contrabands asked for Union protection. On the morning of the 11th Captain Bartholf and his men arrived in town. Bartholf’s men fired the schoolhouse building and its cotton. Sixty men were transported to the Ariel that day. The Rosalie arrived on the 12th to help transport the men. With all the soldiers loaded by the 13th, the three ships headed to Tampa Bay.

In 1855, John L. May built a 4 room home for his wife, Marena, and their two daughters. Unfortunately, John died of tuberculosis three years later. Marena remained in the home throughout the Civil War and eventually married Confederate soldier Frank Saxon. The home was enlarged in 1903.