The Battle of Olustee, or Battle of Ocean Pond, took place in Florida, on February 20, 1864 - and was of course part of the American Civil War. It was the largest battle fought in Florida during the war. Ryan Reidway explains.
The Battle of Olustee by Kurz and Allison.
“In ninety hours we have marched one hundred and ten miles, fought a battle of three hours duration, got badly whipped, and what is left of our little army is back again to where we started from.” Lieutenant George E. Eddy of the 3rd Rhode Island[1].
The battle Lieutenant Eddy was referring to was the battle of Olustee, also known as the battle of Ocean Pond. Located in what is now Baker County, Florida, it was fought on February 20, 1864. It was the largest Civil War battle to be fought within the state of Florida, second only to the Battle at Natural Bridge the following year.
Some historians, such as University of Florida History Professor Sean Adams, claim it was one of the deadliest battles of the Civil War due to the combined casualty rates. 2807 dead, of whom 1861 were Union soldiers and 946 were Confederates. In terms of percentages of total forces committed to the battle, the Union suffered a 35 percent casualty rate and the Confederates suffered a 20 percent casualty rate.[2]
Despite these statistics, it is often an overlooked moment within the history of the Civil War. For instance, when looking through the Library of Congress’s database for the Battle of Vicksburg, there are 8,102 results for books and printed materials. Gettysburg has some 12,997 results. Even the Battle of Meridian, in Mississippi, which ended on the same day as Olustee was fought and had far fewer casualties, has 14,329 results.
Olustee has 793, which signifies the lack of research and general knowledge about the battle. Few books mention it, and even fewer are devoted specifically to it. Which, in itself, is perplexing, considering the results of the Confederate Victory at Olustee had a significant impact on the state for the remainder of the war. The battle marked a firm commitment by the people of Florida to support the Confederacy and meant they would not return to the Union until after the war's conclusion.
Gilmores - Build Up To the Battle
At the beginning of 1864, Florida, which had long been considered a relatively insignificant backwater state within the Confederacy, came into the spotlight. With the fall of Vicksburg the year before, the Confederate Government in Richmond became increasingly dependent on Florida to feed the Confederacy. It was estimated by the New York Times that some 2 million cattle were being shipped from Florida to Virginia and North Carolina to support the Confederate war effort[3].
The Union realized how strategically important the state was becoming to the Confederate War effort. With most of the state’s formal troops deployed to the Tennessee Campaign, and with the militias of the state overextended by late 1863, it seemed like easy picking for the Federal forces. It was estimated that in the entire state, there were only 3000 untested militia men defending the state, and of that, only 1500 were in the region where the Union planned operations. [4]
Commanding what at the time was known as the Florida Expedition, Major General Quincy A. Gilmore outlined the objectives of the campaign as exploiting resources, blocking resources to Confederates, disrupting rail service, and recruiting black soldiers. Of course, with the presidential election of 1864 only months away, Gilmore saw an opportunity to impress his boss, Abraham Lincoln. By launching a campaign in Florida, it could be possible to return the disfranchised state to the Union before voters go to the polls in November.
Union naval raids up and down both coasts, as well as a sophisticated naval blockade of the peninsula, had been successful for the majority of the war. In addition, the Union had managed to take back control of many of its pre-war coastal installations throughout the state, including in Key West, Pensacola, Saint Augustine, and Jacksonville. But to meet the demands of his goals, Gilmore was going to have to venture away from the coast and march his army into the interior of Northwest Florida.
By heading west from Jacksonville, he planned on leading his army along the rail lines of the Florida, Atlantic, and Gulf Central Railroad towards Tallahassee. That would cut off the majority of Florida’s population from the rest of the Confederacy. And so by December of 1863, Gilmore began preparations.
The next month, in January 1864, during correspondence with a superior officer, he bragged about the autonomy the Secretary of War had given him over the campaign. “In regard to my proposed operations in Florida, the Secretary replied that the matter had been left entirely to my judgment and discretion, with the means at my command, and that as the object of the proposed expedition had not been explained, it was impossible for you to judge its advantages or practicability.”[5] It is in this example that we get an example of the hubris that would plague the Union soldiers at Olustee.
Relying deeply on his subordinate commanders, especially Brigadier General Truman Seymour, Gilmore gave the order for Union troops to debark from Hilton Head, South Carolina, to Jacksonville on February 5, 1864. Seymour was ordered to capture the railroad junction in Baldwin.
Seymour's Incompetent Arrogance and Finnegans Luck
5,500 troops under Seymour’s command began their march west on February 6th, 1864. The first few days of the operation were mildly successful. There was very little opposition by Confederate forces, and it appeared as if all of the Confederate artillery positions had been taken into Union control. Baldwin fell very quickly, and Seymour's men were pressing forward towards Sanderson. Communications and a supply chain with Jacksonville were established by the Eleventh.
From the very beginning of the operation, Gilmore’s dispatches argue that he placed a great deal of trust in Seymour and expected him to follow orders without question. Gilmore was impressed by the success of the operation so far, yet he was wary of launching an attack on Lake City (the next major target of the campaign) until he felt more confident that the Union controlled the situation. Skirmishes in Sanderson on February 12 forced Seymour to put the bulk of his force in Baldwin. Gilmore sent for Seymour and demanded that a string of fortifications be built at St. Mary's, Baldwin, and in Jacksonville to shore up Union positions. For the next few days, he reiterated the need to stay on the defensive and not risk offensive maneuvers on several different occasions.
On the 15th of February, after ordering one last time that work was to be continued on the defense networks and for Union troops not to advance any further, Gilmore left Jacksonville and sailed to Hilton Head, South Carolina, effectively leaving Seymour in charge. Almost immediately after his departure, Seymour began preparations to march on Lake City. Historians are not completely sure why Seymour chose to do this. Was it his hubris, or did he believe the Union held the advantage at that point? Even after being beaten back in Sanderson only days before.
Unbeknownst to Gilmore, Seymour, or any of the Union leadership in Florida at the time, the Confederate Commander in charge of the state, Brigadier General Joseph Finegan, had been reinforced. A call went out by John Militon, Florida's Governor, asking for recruits for the militia. At the same time, the soldiers from Georgia were also brought in, and by the time the battle started on February 20, he commanded somewhere between 5,000 - 5,000 troops.
Though he was not the first choice of either Governor Militon or General P.G.T. Beauregard, who commanded the Department of South Carolina, Georgia, and Florida,[6] Finegan knew he had something to prove and began making preparations for a counteroffensive. Before the reinforcements even arrived, he had managed to push Seymour back from Sanderon, forcing him to regroup his forces outside Baldwin.
This dispatch that was sent to Governor Milton, regarding the encounter, highlights the tenacity of Finegan and gives a preview of what could be expected at Olustee. “I captured five pieces of artillery, held possession of the battlefield, and killed and wounded the enemy. My cavalry are in pursuit. I don't know precisely the number of prisoners, as they are being brought in constantly. My whole loss will not, I think, exceed two hundred and fifty killed and wounded. Among them, I mourn the loss of many brave officers and men.”[7]
The Battle
On Wednesday, February 20th, 1884, the unexpected yet crucial battle began. With fresh reserves, a minor victory a few days before, and a willingness to stop the Union advance, Finegan decided to hunker down at the railway station just outside Olustee.
Around six in the morning, Seymour left Barbers Plantation in Sanderson and began his approach directly towards the Confederate Lines. “The US force chose speed over security based on previous actions since the expedition’s landing, when most difficulty with the secessionists was keeping them from escaping.”[8] Seymour had opted to take a direct route westward, following the Florida Atlantic and Gulf Railroad lines.
To ensure success, he sent out cavalry to scout the area ahead of the main infantry formations. An hour later, the first shots of the day rang out as the Union cavalry scouts met Finegan’s cavalry. The Union cavalry prevailed and pressed onward. Unbeknownst to them, Finegan's ultimate goal was to lure the Federal troops within range of his newly constructed fortifications.
Union forces continued through the rest of the morning to follow the railway line leading towards Olustee. Eventually, both sides met each other in the swamp that surrounded the Olustee Railway Station, known as Oceans Pond. This is where the bloody stalemate would take place.
Union forces consisted of the 7th Connecticut and the 7th New Hampshire, as well as the 8th United States Colored Troops. Probably the most famous unit to take the field that day was the 54th Massachusetts, which was made up of African American Soldiers. The unit had made a name for itself after the successful attack on Fort Wagner during the battle of Gimballs Landing the previous year. Though they fought heroically and ultimately stayed behind to allow for the bulk of the union force to retreat, most of them did not finish their training, endured the consequences of poor leadership, and were given subpar weapons to fight.
Confederate forces were made up mostly of Georgia Regiments, including the 64th and 32nd, as well as the famous Gambles Light Artillery unit. Due to the reorganization of artillery pieces before the battle, initial battlefield deaths in the unit, and poor utilization of weapons and general confusion among the troops, Gambles' unit was not very helpful to the Confederate cause at Olustee.
Halfway through the battle, the Confederate troops almost ran out of ammunition. These initial problems with supply columns prolonged the engagement. But by late afternoon, new stockpiles of ammo arrived, and Finegan pushed the assault. He was able to rout the Union forces, and by the time the sun went down, his forces had ousted the federal troops from Oceans Pond. Confederate forces pursued Seymour's troops for almost 36 miles to the east before calling their advance off.
Lessons from Olustee
While it was a defeat for the Union, it did highlight the weaknesses of the Confederate Army. Supply issues, which had existed in other battles throughout the Civil War, were highlighted during Olustee. In fact, after the battle, “as secessionists advanced, they reported taking ammunition from the US dead and wounded on the field and capturing over 130,000 rounds of ammunition that had been sitting at Barber’s Station, the previous US camp.”[9] Major resources had been devoted to the cause, which would plague the state and the Confederacy in months to come.
On the Union side, it proved that the understanding of geography and the enemy's devotion to defending their home should never be second to the whims of egotism. In addition, many of the soldiers in the Union Forces found the battlefields' geographical conditions inhospitable. Fighting in a swamp was new to even the most seasoned of Yankee veterans.
Historians have questioned Seymour’s decision to press forward towards Olustee for 166 years. More remarkable was that despite this defeat, he went on to have a celebrated military career.
The battle, which in some ways was symbolic and in others strategic, proved the commitment of Florida to the Confederate Cause. It also demonstrated the need to reevaluate outdated military protocols regarding cavalry and artillery usage. It represented a moment of pride in how fearless African American soldiers were on the battlefield. Finally, this battle kept Florida in the war a little longer.
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References
Anderson, M. G. (2022). Staff Ride Handbook for the Battle of Olustee, Florida, 20 February 1864. Army University Press. Retrieved June 7, 2025, from https://www.armyupress.army.mil/Books/CSI-Press-Publications/Staff-Ride-Handbooks/
Brigadier General Joseph Finegan, CSA. (n.d.). Battle of Olustee. Retrieved May 28, 2024, from https://battleofolustee.org/finegan.html
Fiegan, J. (1864, February 10). Rebel accounts. Governor Milton's dispatch. Rebellion Record: a Diary of American Events: Documents and Narratives, Volume 8. Retrieved June 07, 2025, from https://www.perseus.tufts.edu/hopper/text?doc=Perseus%3Atext%3A2001.05.0093%3Achapter%3D90
Gilmrore, Q. A. (1884, 7 March). General Gilmores' Report. Rebellion Record: a Diary of American Events: Documents and Narratives, Volume 8. Frank Moore, Ed. Retrieved May 29, 2024, from https://www.perseus.tufts.edu/hopper/text?doc=Perseus%3Atext%3A2001.05.0093%3Achapter%3D90
Lion Heart Film Works. (2020, February 20). Civil War 1864 "Olustee: Battle in the Pines" Full-Length Documentary. YouTube. Retrieved May 29, 2024, from https://www.youtube.com/watch?v=28Ukf7wg0ac
Olustee Battlefield Citizens Support Organization, Inc. (2024). Brigadier General Joseph Finegan, CSA. Battle of Olustee. Retrieved May 29, 2024, from https://battleofolustee.org/finegan.html
THIRD RHODE ISLAND. THE DISASTER IN FLORIDA-ADDITIONAL INTERESTING PARTICULARS. (1864, March 01). Letters, Newspaper Articles, Letter, Newspaper Articles Books and Reminiscences of Olustee. Retrieved May 23, 2024, from https://battleofolustee.org/letters/3rd_rhode.htm
Zombek, A. M. (2022, September 6). The Battle of Olustee. American Battlefield Trust. Retrieved June 22, 2025, from https://www.battlefields.org/learn/articles/battle-olustee
[1] (Third Rhode Island. The Disaster in Florida-Additional Interesting Particulars, 1864)
[2] (Zombek, 2022)
[3] (Lion Heart Film Works, 2020)
[4] (Brigadier General Joseph Finegan, CSA, n.d.)
[5] (Gilmore, 1884)
[6] (Olustee Battlefield Citizens Support Organization, Inc., 2024)
[7] (Fiegan, 1864)
[8] (Anderson, 2022)
[9] (Anderson, 2022)
