The Battle of Olustee: The Largest Civil War Battle on Florida Soil

By Joe Marzo

Common questons: When and where did the Battle of Olustee take place? Why was Florida strategically important to both the Union and the Confederacy during the Civil War? Who were the commanding generals on each side of the battle? What was the main objective of the Union expedition into Florida in early 1864? What is another name for the Battle of Olustee?

Florida’s Forgotten Battlefield

In the quiet pine woods of north-central Florida, near a small lake called Ocean Pond, the sound of musket fire shattered the stillness on February 20, 1864. The battle that unfolded there—the Battle of Olustee—was Florida’s largest Civil War engagement and one of the bloodiest per capita of the entire conflict. It was a clash born from overconfidence, desperation, and the long reach of a war that touched even the most remote corners of the South.

Florida had remained largely on the margins of the Civil War. With a sparse population and few large cities, it was not a place where grand armies usually marched. Yet its cattle, salt, and crops became critical lifelines for the Confederacy. As the Union tightened its grip on the Mississippi River and cut off supply lines in the West, the need to disrupt Florida’s contributions became increasingly urgent.

A Risky Union Gamble

By early 1864, Union leaders saw an opportunity. If they could occupy more of Florida, they could sever Confederate supply routes, recruit freedmen into the Union Army, and perhaps even restore Florida to the Union fold in time for President Lincoln’s re-election campaign. Major General Quincy Gillmore authorized an expedition from Jacksonville westward into the state’s interior. The operation would be led by Brigadier General Truman Seymour, an experienced officer who had fought at Fort Sumter and Antietam.

Seymour was instructed to proceed cautiously. But once he landed at Jacksonville in early February with about 5,500 men—including white regiments from New York, Connecticut, and Massachusetts, as well as Black troops from the 54th Massachusetts, the 8th U.S. Colored Troops, and the 35th U.S. Colored Troops—he became convinced that Confederate resistance in Florida would crumble easily. Ignoring orders to remain near the coast, Seymour advanced toward Lake City, hoping for a quick, symbolic victory.

The Confederate Response

Confederate Brigadier General Joseph Finegan, commanding Florida’s defense, realized what was coming. He called for reinforcements, and help soon arrived in the form of veteran troops from Georgia under Brigadier General Alfred Colquitt. By mid-February, Finegan had nearly 5,000 men entrenched along the Lake City–Jacksonville railroad line near a hamlet called Olustee.

The ground was ideal for defense—open pine forest with enough underbrush to conceal movements, and swampy lowlands protecting the flanks. Finegan planned to lure the Union troops deeper into his trap before striking decisively.

The Clash at Ocean Pond

On the morning of February 20, 1864, Seymour’s army began its march westward from Barber’s Plantation. The column moved through the dense pines, wagons rumbling along the sandy road, soldiers sweating under heavy packs. By early afternoon, Union skirmishers encountered Confederate pickets near Ocean Pond. Believing it to be a minor screen, Seymour ordered an immediate attack.

Around 2 p.m., the Union line advanced into a storm of musket and artillery fire. The 7th Connecticut went in first and was quickly shattered. The 7th New Hampshire followed, only to become disorganized amid the smoke and confusion. As casualties mounted, Seymour sent in more regiments piecemeal rather than massing them for a coordinated strike.

The Confederate line, by contrast, was solid and well-positioned. Finegan and Colquitt shifted units skillfully, plugging gaps and reinforcing weak spots as the battle raged. The 8th U.S. Colored Troops, made up largely of newly recruited freedmen, advanced bravely on the left flank. They fought ferociously, trading volleys at close range, but were eventually driven back under devastating fire.

The 54th Massachusetts, already famous for its assault on Fort Wagner, was held in reserve but soon thrown into the fight as the Union line began to buckle.

Retreat and Heroism

By 4 p.m., the Confederate counterattack was in full swing. Union soldiers, exhausted and out of ammunition, began falling back in disorder. The pine woods echoed with shouting men, wagon wheels, and the thunder of exploding shells. Seymour realized the day was lost and ordered a general retreat toward Jacksonville.

What might have become a total rout was prevented by the discipline and courage of the Black regiments. The 54th Massachusetts and the 35th U.S. Colored Troops formed a rearguard, standing firm under fire as the rest of the army withdrew. At one point, a locomotive loaded with wounded men broke down. The soldiers of the 54th hitched ropes to the disabled train and physically dragged it for miles until horses could be attached—an act of endurance and loyalty that became legendary.

By nightfall, the Union army was in full retreat, leaving hundreds of dead and wounded behind. Confederate troops, exhausted from the day’s fight, did not pursue far. The battle had lasted less than four hours but left nearly 3,000 men dead, wounded, or missing.

Aftermath and Consequences

Out of 5,500 Union troops engaged, about 1,900 were killed, wounded, or captured—a casualty rate of more than 30 percent. Confederate losses were around 950. Six Union artillery pieces were captured, along with wagons, rifles, and supplies.

The defeat at Olustee crushed the Union’s hopes of reclaiming Florida’s interior. Jacksonville remained under Union control, but the planned advance on Tallahassee was abandoned. For the Confederates, the victory provided a rare morale boost in the war’s later years. For the Union, it was a sobering lesson in the dangers of overconfidence.

Many of the wounded Black soldiers who fell into Confederate hands were reportedly executed or left to die. The racial hatred that fueled parts of the Confederate war effort showed its ugliest face in the aftermath of Olustee. For the men of the 8th and 35th U.S. Colored Troops and the 54th Massachusetts, survival meant not only escaping battle but evading a fate worse than death.

Remembering Olustee

In the months that followed, Union forces buried their dead in mass graves. Decades later, only Confederate memorials marked the field. A monument to Southern soldiers was erected in 1912, while the graves of Union troops—Black and white—remained largely forgotten.

Today, the battlefield is preserved as Olustee Battlefield Historic State Park, part of the Osceola National Forest. Each February, thousands of reenactors and visitors gather to retrace the conflict. The pine trees have grown tall again, the air still and quiet, but the scars of that day remain etched in memory.

The site serves as both a history lesson and a reminder: even in a place as seemingly isolated as rural Florida, the Civil War’s fury reached every corner of the nation.

Legacy

The Battle of Olustee did not change the outcome of the war, but it left a lasting mark on Florida’s history. It exposed the limits of Union reach in the Deep South, proved the valor of African American soldiers under impossible odds, and revealed how the struggle for freedom and equality did not end with the battlefield.

In the silence of those woods, where the pines whisper above the graves of men who fought on both sides, Florida’s Civil War story still lingers—a story of ambition, courage, and the heavy price of human conflict.

Sources

• American Battlefield Trust – Battle of Olustee

• Florida Center for Instructional Technology – Battle of Olustee

• History.com – Battle of Olustee

• Association for the Study of African American Life and History – Black Burials and Civil War Forgetting in Olustee, Florida