Dickison was born according to some biographers, in what is now Monroe County, West Virginia, or Virginia around 1820. He moved to South Carolina, at an early age , he later served as a cavalry officer in the state militia. Around 1856, he moved to Marion County, settling near Orange Lake at his plantation "SUNNYSIDE".
Prior to the secession of Florida from the Union, Dickison quietly went about building up his holdings, and by 1860 he was considered a wealthy planter and had four children by two marriages, two sons Charles, and R. L. who served under their father in the Confederate Army.
With the outbreak of the war, Dickison began forming a cavalry company in Marion County it. But before the organization was completed, John M. Martin, a leading citizen of the county offered to join if it was converted to artillery, and was known as the Marion Light Artillery Unit. Dickison agreed to this with the provision that Martin become captain of the company while he served as first lieutenant. Soon Dickison returned to Ocala, after resigning his commission as first lieutenant, and raised his own cavalry company, Company H. Second Florida Cavalry was ready for service in July of 1861. Dickison was elected captain and William H. McCardell first lieutenant.
Another explanation of the formation of the Leo Dragoons states that in May of 1862, The Marion Light Artillery reorganized for the war, as a result of the reorganization Dickison lost his status as First Lieutenant. The blow to his ego and his commanding officer, John Martin who at the request of Dickison wrote Brigadier General Joseph Finegan, the district commander, asking him to make Dickison a quartermaster. Martin stated that the loss of Dickison was not only mortifying, but a pecuniary loss as well.
Dickison left the Marion Light Artillery on May 29, 1862. Luckily, noting was heard on the request to be assigned to the quartermasters appointment, and Dickison on the 2nd of July began to raise the last company needed for the formation of the 2nd Florida Cavalry Regiment. It was mustered in on August 21, 1862. Three days later the company moved to Gainesville to procure arms and equipment. They were stationed in Jacksonville, and then moved to Palatka.
The company was composed of volunteers from Putnam, St. Johns, Marion, Alachua, Clay, Duval, Bradford, Columbia, Sumter, Volusia, Hillsborough, Madison and Nassau Counties. The company never number over 200, however, the Federal Troops always exaggerated the numbers in their official reports.
Most of the equipment that the company used were outdated such as uniforms being supplied by the ladies' sewing societies. firearms were muzzle-loading Enfield rifles, ancient pistols, and varied types of fowling pieces.
The military strategy of Captain Dickison greatly hampered the movements of the Federal troops in the St. Johns River valley. He would strike suddenly, then disappear, only to strike again at a point some distance from the first attack. Union sentries walking their lonely outpost were in dread of these surprise attacks. The constant threat to supply lines as well as lines of communications, made Dickison's company a marked prize by the Union military authorities. Many attempts were made to capture the dashing captain and his command, but the most difficult problem was to locate them. So insistent and continuous were the operations of company "H" along the St. Johns that the Union troops called the territory on the west bank of the river Dixie's-land.
"Although Captain Dickison never attained the historical importance of General Francis Marion of Revolutionary War fame, his military tactics and exploits were similar. The British troops named General Marion, the "Swamp Fox". To Dickison the Union troops were a little more generous--they called him "DIXIE." Often in their dispatches Dixie was reported to be in a trap. Somehow the trap never closed fast enough, and Captain Dickison would be heard from some miles away from the purported trap, harassing the enemy's flank."
Captain Dickison was endowed with the quality of military strategy necessary for leadership in guerrilla warfare. Their territory ran from the Georgia line to the Tampa/ Ft. Myers area. And no part of the territory was safe from their attacks and carefully planned raids-WELAKA, FORT BUTLER, GAINESVILLE, CEDAR KEY, BRADDOCKS FARM, PALATKA, JACKSONVILLE, GREEN COVE SPRINGS, ETC. They patrolled the St. Johns River area, and eastward to the coast. The Federals would remove all boats on the west bank of the St. Johns with gunboats, but the rebel leader crossed the river almost at will. He frequently brought back more prisoners than he had men in his own command. They would ambush Union foraging expeditions, and capture pickets, and stragglers from the battle fields, and often bluffing the enemy into surrendering without firing a shot. Even when he was not engaged in attacking the enemy, the fear was there. Union forces spent most of their time in St. Augustine, or a few of the scattered posts. The Federals could occupy the towns, but they were never able to effectively control the countryside.
"Dixie" had a flatboat capable of bearing only a dozen troopers together with their mounts which he kept hidden in the river swamps so that it usually took him all night and most of the next day to make a crossing.
Palatka, Green Cove Springs, Welaka, and other ports, were important shipping points for the areas around them. Supplies were gathered from the plantations in the vicinity of these ports and landings and shipped to the Confederate armies operating in the border states. Transportation was limited. The Union forces were interested in controlling the rich farming region, and cutting the supplies that the Confederate armies needed in the north. Therefore, the Federals sent in gunboats to patrol the river, so the Confederates moved their headquarters a few miles from Palatka, and waited for the Union troop movements.
One of the objectives of the Union secret agents was to drive the slaves away from the plantations and farms, so that crops could not be harvested, and also for them to join the Union troops. Dickison uncovered this plot and captured many of the runaway slaves, and supposedly crushed a probable slave revolt.
In one 44 hour time period, Company "H" had captured two companies of Federal troops, consisting of 88 infantrymen, 6 cavalrymen, and various guns and other war equipment. They had travelled 85 miles, and returned to their headquarters with their prisoners intact, without a loss of a man.
The next time the action picked up was in May of 1864, when the Union gunboats and transports began to appear on the St. Johns. Dickison was given Lieutenant Mortimer W. Bates with a unit of artillery and 25 men to aid in harassing the enemy.
Dickison and his men split up trying to out maneuver the enemy, they watched from entrenchments around the town of Palatka, and decided to try to intercept the "COLUMBINE" at Brown's Landing.
Dickison took the cavalry troop and the artillery battery and tried to reach their strategic point first, however, as they reached the area, the Columbine was speeding just passed the area. They next waited for the "Ottawa," the largest of the Federal Gunboats and transports on the river. The river was difficult to navigate at nightfall, and the boat anchored fro the night. The Confederates set up their guns in strategic positions, and then they waited, it was pitch dark, however, after a few minutes, the boats lit their torches and made them perfect targets for the Confederates.
The Ottawa was badly damaged. It remained anchored for 30 hours while repairs were made. It was reported that several men were killed and wounded on the boat, however, Dickison reported that not one of his men had been killed.
The next day Dickison ordered Lt. Bates to set up at Horse Landing and await the gunboat, "COLUMBINE". Around 3 o'clock smoke from the vessel was seen. Dickison permitted the gunboat to approach within 60 yards of the wharf, and then he gave the order to fire. The attack was so sudden that the men aboard panicked. After the second volley of fire, the boat was rendered helpless, it floated on a sandbar and stuck. A fight lasted for 45 minutes but the first two volleys had won the fight. The flag of surrender was hoisted by the Union forces.
Dickison sent Lt. Bates on board to accept the surrender. He found that of the original 148 men, only 66 remained, and 1/3 of these were badly injured. After the dead and wounded were removed, Dickison ordered the craft burned. Dickison scored another military success against great odds. Not a single man was lost in the attack. One man was slightly stunned by the explosion of a Union shell.
Dickison presented Lt. Bates with a handsome sword that was taken from a Union officer as a token of his appreciation of the marksmanship and bravery of the battery.
One of the officers captured was Major General Foster, who was in command of the Federal forces operating in the St. Johns River valley. He told Dickison that there was a major effort to capture or destroy Dixie, and that two regiments had disembarked at Palatka, and were scouring the countryside looking for Dickison and his command.
Dickison received a message that the Union forces had landed and seized Palatka. Dickison returned to Palatka and after evaluating the situation, requested headquarters to send him additional forces. After a short skirmish with the Federal cavalry, the Confederate troops retreated, Dickison lost three of his men who were captured, and the enemy seized his camp. The Federal cavalry pursued for about 1/2 mile, and they gave up the chase.
The Union cavalry battalion numbered 280 strong, they were better equipped, and out numbered Company H. Dickison continued to advance, and they were forced slowly back to Palatka, some six miles away. A number of the union soldiers were captured, Dickison with 30 men engaged in a hand to hand battle. During a lull in the firing, Sergeant Charles Dickison thought there was an intent to surrender, and proceeded to advance, suddenly the Union forces opened fire and he was mortally wounded, his body was taken to Orange Springs, and the ladies of that community buried him. This was one of the best examples of individual military strategy, and leadership during the War. HE drove the enemy to within hailing distance of the Union garrison at Palatka, where 2,000 troops were stationed, the Union force lost 14 killed, 30 wounded, 28 captured, and Dickison lost 1 killed, and one wounded.
After the Battle of Palatka, "Company H" was returned to picket duty along the St. Johns River.
Two more major battles soon followed, the Battle of Gainesville, and Waldo.
The end of the War found Dickison at Waldo. He surrendered and was paroled at Waldo on May 20, 1864, still a captain despite repeated efforts by his superiors to get him promoted. A few days later, Secretary of War, John C. Breckinridge of C. S. A. arrived at Gainesville, carrying his appointment as a colonel.
He was also instrumental in aiding and abetting the escape of Breckinridge to Cuba after the War. He had been asked to accommodate the fleeing President of the C. S. A. , Jefferson Davis, however, Davis was captured in Alabama* (it was near Irwinville, Georgia -- Only 70 miles north of the Florida state line !!!) before he could make it to the safety of the Florida Swamps, and the elusive Confederate Swamp Fox.
Dickison was idolized by his men, and became one of Florida's greatest heroes of the war. In 1864, the Florida Legislature voted Dickison and his command their thanks. Major General Sam Jones, Brigadier Generals Joseph Finegan, and John K. Jackson. Dickison commanders, repeatedly commended him and urged his promotion. Only the Confederate War Department bureaucracy kept him from obtaining a well earned colonel before hostilities ceased.