Immediately following the above orders, the Union Steamer Honduras carried General Woodbury and his troops from Forth Meyers to Tampa where they met the above mentioned naval vessels.  With a joint expedition the U.S. Navy and the U.S. Army met at Tampa for the purpose of a raid.  On the afternoon of May 5, 1864 navy vessels carried General Woodbury, the 2nd FL. Calvary and two companies of colored troops to land.  On the morning of May 6, 1864 these Union Troops carried out a raid on Tampa and took possession of that place capturing 40 rebel prisoners and hoisting the Stars and Stripes in the town that had been under Confederate command the day before.  In addition to making a raid on the City of Tampa it was reported on May 14th, 1864 by Confederate Major General Patton Anderson that Union Troops had also carried out their first raid on Hernando County.  

It was on May 14, 1864 that the Confederate States Army had received word from Brig. General Joseph Finegan, that in addition to the raid on Tampa, the village of Brooksville had also been completely destoryed by the raiding Union troops.  Major General Anderson who was given command of the Florida District and was responsible for filing reports giving details as to the forces in his district and under his command.  Under Major General Anderson was Brig. General William M. Gardner, sub-district no. 1 of Florida, and Brig. General Joseph Finegan, sub-district no. 2 of Florida.  Hernando County and south of the Chasahowitzka River was apart of sub-district no. 2 under Brig. General Finegan.  On May 14, 1864 Major General Anderson reported and filed an 8 page report where he detailed that "on May 6th Union troops landed at Tampa and arrested several citezens, but what other acts were perpetrated by them I have as yet been unable to learn.  On the following night they [the raiding Union] are reported to have destoryed the village of Brooksville, but this needs confirmation."  This was the first reported land raid on Hernando County and the village of Brooksville.  The reports of Brooksville being completely destoryed in May of 1864 proved to be unfounded and false and Anderson further clarified this in his report by saying, "since ascertained to have been without foundation"  The ever impending doom of a Union raid was fresh on the minds of Hernando residents and the Confederate States Army as reports of the Union troops making their way north to Hernando were starting to come in.  Below is an excerpt taken from Major General Anderson's report filed on May 14, 1864 detailing the village of Brooksville being destroyed.


After their raid the Union troops were sent back to the U.S. Military post in Fort Meyers and by June of 1864 the U.S. Navy and the U.S. Army were making plans for a joint expedition to carry out a raid on Brooksville and Hernando County.  On June 25, 1864 the Schooner Ariel, Sloop Rosalie and Schooner Stonewall all received communication from Capt. J.W. Childs, commanding officer of the U.S. Army Post at Fort Meyers, requesting the means of transportation of 250 troops to a point convenient to Bayport.  The object of the planned expedition was to make a raid on Brooksville and then fall back on Bayport, where the troops could be extracted after the raid.  On July 1, 1864 the three schooners took on board the companies of the 2nd Florida Regiment [Union] and the 2nd U.S. Colored Troops consisting of 240 men, under the command of Capt. J.W. Childs.  While at sea the wind and rains were rough, on the day of July 4, 1864 the boats anchored and there was no sailing for the celebration of Independence Day.  On the 6th day at sea the vessels finally reached their destination of Anclote Key where the troops would be detached, on July 6, 1864 at 5 p.m. the Schooner Ariel, Sloop Rosalie and Schooner Stonewall anchored just off Anclote Key to await daylight.

On the morning of July 7, 1864 the consort boats spent the better part of the day running troops from the three schooners anchored just off Anclote Island to the mainland where they would march toward Brooksville.  With the troops loaded on the small consort boats conditions were cramped and men had to lay across and atop one another for the entire trip.  By 3 p.m. in the afternoon most of the troops had made their landing on the north side of the Anclote River, Captain Childs and 8 men being unable to march remained on board the Schooner Ariel for a return trip to Tampa, along with the Sloop Rosalie and Schooner Stonewall.  While the three schooners were ordered to return to Tampa, orders were given to the Schooner Ariel to meet the troops at Bayport on July 12, five days after their departure from Anclote.  Having been at sea for the better part of a week, once landed the men could finally make a fresh cup of coffee and straighten themselves from their lengthy trip at sea from Fort Meyers.  Once all the troops were landed on the north side of the Anclote River, the orders were given and the 240 Union men immediately formed ranks and took up their line of march.  The men marched until about 8 p.m. that night when orders were given to make encampment for the night.  Having marched the short distance of 3 miles north of the Anclote River the Union Troops stopped their line of march and camped for the night.

At 3 a.m. on the morning of July 8, 1864 the Union encampment awoke early to discover the smoke of a camp fire ahead of them to the north.  The Union Troops were immediately order to form their ranks and prepared to take up their line of march toward Brooksville.  While the troops were falling into ranks and making preparation for the days march an advanced guard was formed consisting of 10 men who were under the command of Capt. Henry A. Crane, a few years prior in 1860 Crane had been the supporter of secession but soon sided with the Union.  Eventually the 240 Union Troops picked up their line of march for the day with their advanced guard ahead of them.  As the advanced guard made their way towards Brooksville, just after sunrise they encountered the first Confederate pickets that had been set along the roads.  The Union's Advanced Guard had surprised the Confederate picket originally comprised of 18 old men and young boys.  Being surprised by the Union's Advanced Guard more then half of the Confederate picket retreated, resulting in the capture of 7 men and 9 horses with their supplies of guns and ammunition.  While these men were captured they put up a strong resistance.  As a result of the Confederate resistance one of the men on the Union's Advance Guard was slightly wounded in the ankle.  This small skirmish and first Confederate picket was located approximately 25 miles southwest of Brooksville.  By noon the Union Troops, advancing on Brooksville, captured 3 more rebels at their homes where the troops also paused and had a brief dinner.  After dinner Union Troops advanced another 3 miles when Capt. Daniels fell sick and the advancement was ordered to halt.  As the Union advancement halted a small party of men was ordered to return to the home, where they had paused for dinner, to retrieve a cart for the ill Capt. Daniels.  Here, the small party of men comprised of U.S. Colored Troops behaved most outrageously to the families as they entered the house and tore the children's and women's clothes to rags.  In addition the men took a ring from one of the small girls, which had been sent to her by her brother.  As the men left with the cart they had been sent for, they took with them the tin ware and broke a crockery and pots completely raiding the home.  It was finally decided to set encampment for the night and the Union Troops didn't march any further.

On the morning of July 9, 1864 the Union encampment broke as the men were once again ordered to form their ranks and prepare their line of march toward Brooksville.  Having marched the short distance of 3 miles from their encampment, with the Union's Advanced Guard 2 miles ahead of their mainline, they encountered a Confederate patrol.  Just as the day was breaking, Hernando County residents Thomas Benton Ellis, Walter Delany and John Crichton were on patrol with Capt. Leroy Lesley's home guard and the picket that had been set along the road leading to Brooksville.  As Capt. Ellis saw the Yankees coming up the road they were riding the Confederate horses that had been captured in the skirmish the day before.  Ellis immediately sent Capt. Delaney at once towards Brooksville to give warning to the remaining members of Capt. Leroy G. Lesley's Home guard Company of old men and young boys.  As Capt. Delaney reached Brooksville, a runner was sent at once to Tampa to have the companies of Capt. John T. Lesley and if possible Capt. McKay's detailed men to come immediately and assist in the protection of Brooksville against Union Raid, the runner left at full speed.  As the runner left for Tampa, Capt. Leroy G. Lesley's Company of old men and young boys were at once to come to a creek or branch situated about 20 miles from Brooksville.  The men were ordered to form themselves along the creek as Capt. Crichton and Ellis would try to hold the Yankees in check as best as they could.  While riding their horses backwards, Capt. Ellis and Crichton stayed just ahead of the Yankees allowing them to get within speaking distance.  Capt. Ellis recognized the Yankee pilot leading the Advanced Guard as a deserter who was also one of his neighbors, a man named Hancock.  The Yankee named Hancock hollered to Capt. Ellis and told him to stop as they would not hurt him, however Ellis didn't believe the deserter and continued in front of them.  At times the two parties were only 100 yards distance from of each other but neither party fired nor advanced but instead held their position yelling back and forth as they slowly advanced along the road, each side with their own plan.

After about 1-1/2 miles Capt Ellis and Crichton reached the creek where they had ordered Lesley's Home guard to form themselves and prepare to engage with the advancing Union Troops.  By this time the main body of the Union Troops had caught up to the Advanced Guard.  As Lesley's Hom guard had prepared themselves along the creek, they were not prepared for the advancement of 240 Yankees that they saw marching down the road toward them.  Capt Ellis noted the men on the other side of the creek were running all about helter skelter with no one and everyone in command, as some of the men ran back to their plantations to run off their slaves.  Capt. Ellis immediately saw that he couldn't really do anything to check and hold the advance of the Union Troops on Brooksville however, Ellis wasn't going to go down without a fight.  Just as he had ordered as soon as he reached the creek, Ellis turned his horse and fired on the advancing Union Troops.  The Union Troops soon formed their skirmish lines and immediately sent out a flank party of 30 men to combat the rebels.  Under the protection of the flank party Union Lieut. John Miller moved the white troops forward to within 20 yards of the creek, leaving the Colored Troops back as reserves along with the prisoners captured the day before.  Eventually the Union's main body crossed the ford in the creek and in single file poured their volleys towards the Confederates driving them back about 400 yards.  The Confederates soon took refuge behind a large pond where the fire of the Union Troops couldn't reach their lines.  As the two sides skirmished the Confederates eventually pulled out and retreated to Brooksville likely to prepare for the arrival of the advancing Union Troops upon the town.

As the Union Troops advanced along the road leading to Brooksville they eventually reached the plantation and home of Capt. Thomas Benton Ellis where the troops halted for breakfast.  Ellis' mother, Sarah Townsend Ellis, being home with the children of the family, fed the Union Troops in hopes that they would not burn their home.  Here at the Ellis Plantation the Union Troops spent several hours feeding the men from the plantation smokehouse, pantry, barns and corn cribs eating chickens, eggs and as much honey as each man wanted.  The Union Troops also took the plantation wagons loading them up with supplies and food.  After breakfast the Union Troops again formed their ranks and prepared to take their line of march toward Brooksville.  As the troops prepared to leave the Ellis Plantation they set fire to the barns, smokehouses, corn cribs and servant houses in addition to the house with Sarah Ellis and the children inside.  Capt. Ellis tells, that as the troops marched away from their plantation one of the deserters, a Methodist preacher and neighbor, slipped to the back of the Ellis home and snuffed out the fire, which was well underway.  The Methodist  preacher was kind and told Mrs. Sara Ellis that nothing in her room would be disturbed as he slipped into the other rooms of the house taking certain articles from each, it is not known if the preacher and neighbor snuffed the fire for the family or for his own personal benefits.

As the Union Troops marched toward Brooksville they were once again met with resistance from the local rebel home guard.  The Union pulled their best marksmen and placed them at the front, soon after the rebels pulled back but continued to skirmish throughout the day.  Towards the evening Capt. Leroy G. Lesley rode his horse out onto the lines that had been formed, carrying with him a flag of truce.  Lesley rode out with the purpose of inducing, a one Capt. Green and other Union Officers, to desert the Union cause and move back to the side of Dixie.  The Union Officers immediately let Lesley know "that they would not listen to nothing of that kind" and broke the conference dismissing Lesley and his flag of truce.  Being insulted at Lesley and his offers of desertion, the Union immediately took their line of march toward Brooksville again skirmishing with the Confederate Home guard along the way.  By nightfall the Union Troops had reached the plantation of David Hope, it was decided that the march would halt for the day and encamp and the plantation David Hope.  Here at the Hope plantation the Union Troops helped themselves to the chickens, ducks, geese, a quantity of yams, plenty of mutton corn, an entire barrel of bacon and a cache of syrup; the men didn't spare anything.

On July 10, 1864 while the Union Troops were encamped at the plantation of David Hope and preparing to take up their line of march for the day, the Union Schooners Seabird and Ariel left Tampa sailing for Bayport as previously ordered upon the departure of the Army troops from Anclote on July 7.  The Seabird being unable to navigate the shallow waters of Bayport anchored about 4 miles from the town and prepared a small boat with 10 armed men.  In the meantime Ariel had stood in for Bayport running within 100 yards of the battery where they pulled up and anchored, observing a few men retreating from Bayport by road.  After Ariel had anchored at Bayport, Acting Ensign Bacon, was then dispatched to reconnoiter under a flag of truce and demand the surrender of the town if he found anyone still there, or to take possession if they had evacuated.  When Acting Ensign Bacon returned he reported that all the male inhabitants had fled leaving only the women and children, consisting of five or six families; all residents of Bayport.  Bacon also reported that there were a few bales of cotton, located on the wharf, ready for shipping.  The Ariel was soon joined by the smaller boat of the Seabird and its 8 armed men along with the Seabird's Captain Robbins and Acting Ensign Dunderdale.  These 10 men along with U.S. Army Capt. Childs, were immediately dispatched on shore where 6 of the 10 soldiers began the duty of setting pickets along Bayport's main road.  

As the Union Officers landed on shore they proceeded to examine Bayport, visiting the families who were greatly frightened while claiming they had no knowledge of the expedition that was operating against Brooksville.  These families also assured Union Officers that only two vessels had run the blockade from Bayport within the last five months.  The two guns that had been situated on the Bayport battery and had been used against the Union Blockade Squadron the year before, had been removed to Brooksville for sometime indicating that perhaps residents did have knowledge of the operation against Brooksville.  Officers seized 11 bales of cotton located on the wharf and ready for shipping , which was sent on board the Ariel.  There was also 20 to 30 bales of loose cotton lying in the building formerly used as the Bayport Schoolhouse and 32 bales of cotton on the road about a mile and a half from the wharf, this cotton was ready for shipping.  There was also a number of large scows and small boats used to move cotton and goods up and down the rivers, however there were no blockade running boats.  Four slaves had also placed themselves under the protection of the Union Officers and they too were seized as contraband.  After a thorough examination of Bayport extra pickets were stationed along the main road with strict orders not to enter a house or molest anyone, the Union Troops then settled themselves and awaited the next day.

Meanwhile, the Union Troops situated near the plantation of David Hope again took up their line of march toward Brooksville.  As the troops departed from Hope's plantation they proceeded in burning all of the building located on the plantation property, which included the smokehouses, corn cribs, servant house and barns.  While it is believed the Union Troops spared the home of David Hope, it is believed that they pillaged the home taking anything they wanted.  At 11 a.m. the Union Troops halted their line of march to take a break and have dinner, this was 1-2 miles from their destination of Brooksville.  While the Union Troops paused and had lunch it was determined that Brooksville was completely deserted.  As some argument between the officers had occurred, it was decided to change the first intentions of raiding Brooksville.  The Captain of the 2nd U.S. Colored Regiment, Capt. Bartholf, was convinced against the raid of Brooksville, perhaps from the earlier conduct of his men, and would not proceed to the town.  At 3 p.m., 4 hours after halting their line of march, the Union Troops were turned and recommenced marching not toward Brooksville but towards Bayport, some 18-miles distance.

As the Union Troops marched towards Bayport they reached the plantation of William B. Hooker, located 3 miles from the David Hope plantation.  Here the troops met Mrs. Hooker who informed the officers that Mr. Hooker was absent as he was carrying away his slaves to avoid being captured during the raid.  Mrs. Hooker saved the sacking of her home by furnishing Capt. Bartholf and his officers of the colored troops with dinner and a change of shirts, the refugees and their officers refusing.  The men however did accept melons, which they found in abundance at the plantation.  After spending 2 hours enjoying their refreshing treats the troops commenced their march and soon came to the plantation of Aaron T. Frierson.  The troops spent very little time at the Frierson plantation, however the burned the fences and all the houses as the marched through.  As they continued their march toward Bayport they soon came upon the plantation and home of Capt. Leroy G. Lesley.  Here the Union Troops once again sacked the corn cribs, wagons and barns setting fire to everything.  Mrs. Lesley met the Union Officers with a flag of truce and begged them to spare her life.  Capt. Batholf thought that it was best to do so but allowed the black troops to pillage and sack the Lesley home.  As the colored troops marched toward the Lesley home the Confederates were lying and waiting in the brush near the home.  The rebels skirmished with the small body of Yankee troops until their main body of troops came up to offer support, at which time the rebels pulled back.


After the sacking and burning of several plantations the Union Troops continued their line of march towards Bayport.  Since the troops had spent so much time enjoying melons and sacking the plantations they continued their march well after nightfall.  Shortly after dark the Union Troops located about 4 miles from Bayport decided to encamp along the road when a lone Confederate soldier mistook the encampment for his own.  Here the lone Confederate soldier shared what information he knew with the Union Troops, after which he was released with orders to hurry to Capt. Ellis and Capt. Lesley informing the captains that they might capture the Union gunboats at Bayport if they hurried.  The Union Troops were trying to lure the Confederate to their encampment, however an hour after the man was released he returned to the Union encampment, lost.  Upon the lone Confederates second approach to the Union encampment he was fired upon but was missed and it was thought best to retain this man before he was killed.  After consultation the Union Officers thought it was best to break up their encampment and move to the swamps where they could form a line of battle for protection..  At a half mile from the swamp the Union Troops heard the horse pickets of the Confederate Home guard who were on their patrols of the area.  The Union march was so cautious that the Confederate picket didn't hear them although they passed within 50 yards of each other.  After the Union Troops reached the swamp where they had relocated their encampment, the main command laid flat upon their arms while their skirmish pickets were positioned in the front with 50 men lying in wait along the road.  With the Union Troops in position, at about 10 o'clock that night the Confederates appeared on the road before the Union pickets.  The party of Confederates on the road proved to be the company of Capt. Leroy G. Lesley.  As the young Capt. John T. Lesley also approached he was fired upon by his own father who mistook him for a Yankee, Capt. John T. Lesley was wounded in the in the shoulder and arm but was not killed.  However, the gun fire from Capt. Leroy G. Lesley did kill a Yankee prisoner who was with the young Lesley as he approached.

On the morning of July 11, 1864 the Confederate Home guard and pickets pulled their company out from Bayport and headed back to Brooksville as the raid was nearing the end.  The Union Troops continued their line of march for Bayport and at about 10 a.m. they reached the town.  As the troops came in and took possession of Bayport the pickets that were stationed along the road by Capt. Childs, several days prior, were removed.  The commanding officer ordered a party of detailed men to assist in getting the cotton to the wharf to be loaded on the boats.  When the advanced guard reached Bayport they established a post at one of the houses.  Before the guard got around the town to all the families, a members of the 2nd U.S. Colored Troops had gotten to the home of Confederate Capt. John Parsons.  The Parsons' House was sacked and all the furniture broken up by the Union men and was said to have been done since Capt. John Parsons had sent the lost man to the Union encampment the night before.  This man had been sent to Capt. Lesley to let him know about the arrival of the Union gunboats at Bayport.  Capt. John Parsons was the man that the Union gunboats had seen escaping upon their arrival to Bayport.  Parsons saw the Union boats entering the Harbor of Bayport and escaped up the salt creeks warning the Confederate home guard stationed at near Brooksville.

Once the Union Troops had secured all the houses and families of Bayport they began to gather all the cotton and any useable provisions, which was to be loaded on the boats for transport.  Cotton was gathered from a site along the road just outside of town and from the former schoolhouse, after which it was taken to the wharf where it was baled.  Once all the cotton was gathered it equaled approximately 140 bales, however there was about 40 bales accidentally burned during gathering.  During the gathering process one of the guards, while lighting his pipe, set fire to a large batch of the loose cotton, consisting of about 40 bales in total.  At 5 p.m. with all the cotton loaded on the Schooner Ariel orders were given to the troops for them to withdraw from Bayport, this would be a slow and somewhat steady process.  Not only did they have to transport the army troops but they also had the additional cargo of cotton, prisoners, and captured slaves; which they didn't have on their incoming trip.  The Schooner Ariel took 60 men and transferred them to the Schooner Seabird, which was anchored and waiting just off shore.  These would be the only men transferred on this day as nightfall soon came and it was too dark to carry out any further duties.  The Union Troops actually set encampment in Bayport for that night.  This was the only time during the war that Bayport was under control of Union Troops, Brooksville NEVER fell to Union control.  Brooksville was among the few Confederate controlled cities in Florida who remained under Confederate control for the entire war.

On the morning of July 12, 1864 the Schooner Rosalie arrived and anchored just off shore near to Seabird as the Schooner Ariel transported the troops from the Bayport mainland to the waiting vessels.  In addition to the Ariel transporting troops there were several smaller launch boats that also carried troops, the entire day was spent transporting troops from the mainland to the schooners anchored off Bayport.  On the morning of July 13, 1864 both the 2nd FL Calvary and the 2nd U.S. Colored Troops, consisting of 240 men, had completely withdrawn from Hernando County and were situated just off the coast of Bayport aboard the Schooners Rosalie, Seabird and Ariel.  Before pulling their anchors and leaving, James J. Russell, Acting Master of the Schooner Ariel, destroyed the building used as a customs house, all the boats, scows and cotton storage house.  With the Port of Bayport burning the three schooners left Bayport and set sail for the U.S. Military Post in Fort Meyers where they had departed from a week prior.  However, the Schooner Ariel made a stop once again at Anclote Key for the purpose of storing the cotton captured at Bayport.  By leaving the cotton at Anclote Key there would be more room aboard the schooner for the army troops who were already cramped.  After leaving the cotton at Anclote Key the Schooner Ariel proceeded to Tampa and there transferred all the troops and prisoners to the Steamer Ella Morse.  The Schooner Ariel then returned to Anclote Key to retrieve the captured and prized cotton that was stored at that place earlier.  The 240 Union Troops would return to the U.S. Military Post at Fort Meyers on July 14, 1864.

Within days after the Union Troops withdrew from Hernando County the Confederate reinforcements arrived from Tampa.  Leslie's and McKay's Companies had started from Tampa as soon as they got the message from the runner but the runner had to ride 50 miles to Tampa and the Companies had to come 50 miles back, making it a 100 mile trip.  Arriving too late these two companies began to prepare for plans of making their own raid against the Union at the U.S. Military Post at Fort Meyers.

After the Brooksville-Bayport Raid
With several plantations throughout the Brooksville area being destroyed from the Union raid and the East Gulf Blockade Squadron keeping up their increased activities, residents had to endure many new hardships including the process of rebuilding.  Prior to the raid, life was difficult due to the lack of food throughout the county while the raid itself destroyed what little food was left leaving Hernando County in total disarray.  After the Brooksville-Bayport Raid was completed the East Gulf Blockade Squadron continued their efforts in the blockading of vessels off the coast of Hernando County further keeping goods and food from reaching the residents.  After Union Troops were returned to the Fort Meyers Military Post, the Schooners Rosalie, Ariel, and Seabird returned to their duties of blockading the coast.  By October 1, 1864 the Schooner Seabird, being assigned to the U.S.S. Hendrick Hudson,  made a capture of a British Schooner loaded with an assorted cargo, the following report was filed upon the schooner's capture: