On December 22, 1863, Major General Quincy Gillmore, commander of the Department of the South, received approval from General-in-Chief Henry Halleck to send a force into the state of Florida to cut off Confederate food supplies and recruit Negro troops. By this time Florida had become the major supplier of beef and bacon for Confederate armies in Tennessee, Georgia and South Carolina. In addition, exiled loyal Union men from the state, such as Federal Tax Commissioner Lyman Stickney, were pushing President Lincoln to reestablish a loyal state government in Florida. On January 13, 1864, Lincoln sent General Gillmore a message that he should accomplish this in the most speedy way possible and that he would be sending John Hay, his personal secretary appointed to the rank of Major, to accompany the expedition and aid in the process. Anticipating a close election in the fall of 1864 where he would be challenged by the man he had fired as head of the Army of the Potomac, General George McClellan, Lincoln could use all the electoral votes possible. Gillmore informed Halleck the next day that the final decision had been made to occupy the west bank of the St. John’s River. Oddly, Halleck responded that Secretary of War Stanton informed him that Gillmore should act at his discretion since neither Stanton nor the Secretary of the Navy had been informed of the objectives of the operation, seeming to imply that the expedition was being directed by the President. Gillmore ordered Brigadier General Seymour to proceed to Jacksonville from Hilton Head with six regiments of infantry, one regiment and battalion of cavalry, and three batteries, a total of 5,000-6,000 troops. They landed there unopposed on February 7th for what would be the fourth Union occupation of the city.

General James Finegan commanded Confederate forces in eastern Florida with only 1,800 infantry, 450 cavalry, and two batteries, less than half the size of the Union forces that had arrived. Finnegan was quickly made aware of the Union landing and notified the general commanding the Department of South Carolina, Georgia and Florida, General P.G.T. Beauregard of the situation on the 8th. Beauregard responded quickly that Finnegan should delay the Union troops with the men he had available until reinforcements from Charleston and Savannah could be sent. Finnegan began the process of concentrating the men he had at Lake City.

On the evening of the 8th Colonel Henry commanding a detachment of the 40th MA was sent west on a raid. They approached the camp of the Milton Light Artillery who fled, and rode into Baldwin, 20 miles from Jacksonville, at sunrise without firing a shot. Baldwin was the junction of the Florida Railroad and the Florida Atlantic and Gulf Central Railroad. By this point they had already captured 100 prisoners, eight cannon with ammunition and large stores of provisions. By sunset on the 9th they were at Sanderson. They continued west to within a few miles of Lake City where they ran into a Confederate force of 490 infantry, 110 cavalry and 2 guns and after a brief skirmish the Federals returned to Sanderson. Colonel Henry’s men had penetrated 50 miles into the interior, seized or destroyed $1,000,000 dollars in Confederate property and identified the main body of the Confederate army at a cost of five Federals killed and 10 wounded. General Seymour based on his brief experience in Jacksonville telegraphed Gillmore that there was no strong support for the Union in the area and that Stickney and others had misinformed Gillmore and Lincoln. Seymour recommended that forces should advance no further than the rail hub at Baldwin and that only the towns of Jacksonville and Palatka (over 60 miles away) should be held. General Gillmore came to Jacksonville on February 14th and left very specific orders for Seymour to fortify Baldwin and some sites along rivers but to not advance west of Baldwin toward Lake City without his approval.

General Finnegan, expecting another Union movement west, had selected a position to defend that was between two lakes where each flank was protected by swamps. A dirt road and railroad ran east to west through this gap. The Confederates constructed entrenchments and awaited reinforcements (area of the red circle in the map below). Beauregard was responding quickly moving regiments from Charleston and Savannah. By the time of the battle on February 20th regiments commanded by Brigadier General Alfred Colquitt and Colonel George Harrison had arrived from South Carolina and Georgia. The Confederates would have available 4600 infantry, a little less than 600 cavalry, and three 12-gun batteries. General Colquitt would command the 1st Brigade made up of the 6th, 19th, 23rd, 27th and 28 GA, the 6th FL, and the Chatham Artillery. Colonel Harrison led the 2nd Brigade consisting of the 1st FL, the 1st, 32nd, and 64th GA, the 28th GA Artillery, Gamble’s FL Artillery, and Geurard’s Battery of GA. Colonel Caraway Smith commanded the Cavalry Brigade (2nd and 5th FL, and the 4th GA Cavalries).

General Gillmore headed back to Hilton Head when on February 17th Seymour completely on his own suddenly had a change of heart and announced to his men a plan to capture Lake City (60 miles away) and the railroad bridge across the Suwannee River (95 miles away), and control the eastern approaches to Tallahassee. Upon arriving back at Hilton Head Gillmore had two telegrams awaiting him from Seymour declaring his plans for the expedition which by this time was already underway! He also asked Gillmore to request that the Navy conduct what he viewed as an essential diversionary raid into Georgia to prevent reinforcements from being sent to Florida from there. Gillmore responded in a harshly worded telegram stating that he had no authority over the Navy and could not possibly arrange such an operation with Admiral Dahlgren in such a short period and that Seymour had ignored all of his instructions as to what was to be done in Florida. He also pointed out that his proposed operation was moving too far into the state, without plans for provisions, far beyond the point of the previous raid which had to turn around for that very reason. He made it clear in no uncertain terms that Seymour’s action were rash and irresponsible. Unfortunately, by this time Seymour and his men were already well on their way to Olustee on a road that paralleled the Florida and Atlantic-Gulf Central Railroad. By the 19th they were at Barber’s Plantation.

From this point the battle is very well interpreted by the signs on the 1.1-mile loop walking trail at the Olustee Battlefield Historic State Park. I have excerpted text from the signs there and maps from the book Confederate Florida by William Nulty to summarize the battle.

The Union army with 5,500 men and 16 cannons, commanded by Brigadier General Truman Seymour, left Barber’s Plantation (near present-day Macclenny) at 6:00 AM. They crossed the St. Mary’s River and headed west expecting to defeat the Confederates 32 miles away in Lake City. If successful they planned to cut off communication between east and west Florida by destroying the railroad bridge over the Suwannee River further west. Confederate commander, Brigadier General Joseph Finegan, and his force of 12 cannons and about 5,000 men were at Olustee awaiting the Federals. After learning of the Union movement, Finegan ordered cavalry and infantry to advance. As skirmishing intensified, Finegan ordered General Colquitt forward to feel out the enemy’s strength. By early afternoon Union cavalry had driven the Confederate cavalry west for several miles. As the Union neared the railroad station at Olustee Confederate resistance increased.

When the two armies met in force, the Union troops were positioned between two swamps. There was very little cover in which to hide. To the north was an old, cleared field where later the fighting would be severe.

Around 2:00 PM Union troops reached a railroad crossing east of Olustee. Here they faced increased resistance from advancing Confederate troops. The 7th CT opened up with heavy fire from their Spencer repeating rifles catching the 64th GA off guard killing all of their regiment’s field officers. General Colquitt’s reinforcements arrived in time to keep the 64th from being cut down. The 7th CT advanced farther forward and soon found themselves in a crossfire. When their ammunition ran low, they withdrew several hundred yards to the rear. Here the Union advance was finally halted.

By 3:00 PM the 7th NH deployed on the Union right battling heavy fire from the Confederates. Colonel Hawley, in leading the 7th NH, either gave a wrong command or his command was misunderstood. The confusion caused the 7th to scatter and drift to the rear. The 8th U.S. Colored Troops with no battle experience and little training were now on the Union left flank. They had less than one month’s service and had never practiced firing their weapons. They were severely mauled at a railroad crossing east of Olustee. Of the 575 men in this troop, 310 were killed or wounded.

This is the excerpt from Harley’s official report regarding the order “1 distinctly ordered the 7th NH to deploy on the eighth company, which would have brought the left of the line near the pond. Somebody must have misunderstood the order, for a portion of the regiment was going wrong, when myself and staff and Colonel Abbott repeated it vigorously, but vainly. All semblance of organization was lost in a few moments, save with about one company, which faced the enemy and opened fire. The remainder constantly drifted back, suffering from the fire which a few moments’ decision and energy would have checked, if not suppressed. Most of the officers went back with their men, trying to rally them.”

Around 3:00 PM Colonel Harrison arrived with Confederate reinforcements and General Colquitt ordered the troops to advance. Colonel Barton’s brigade for the North was soon subjected to concentrated fire in the area recently vacated by the 7th NH Hampshire. At this point in the battle, the Union had five cannons captured and nearly every other cannon was rendered useless (their horses and men were nearly all killed or wounded). A train of cars arrived bringing reinforcements for the Confederates. General Colquitt had a large cannon mounted on a railroad flatcar which shot a large shell every five minutes, devastating Union troops.

The 54th MA and the 1st NC U.S. Colored advanced, staggering the enemy for a moment. Around 5:00 p.m. the fire slackened on both sides as soldiers were running out of ammunition. The men searched the pockets of their fallen comrades, desperate for ammunition. New supplies of ammunition arrived for the Confederates. The entire line moved forward, led by the 27th GA, driving the Union forces from their positions.

After three hours of fighting, every regiment except for the 115th NY had been compelled to leave the field. At darkness fell they were ordered to the rear. The Rebels continued the pursuit for several miles, when night put an end to the conflict. The Federals reached Barber’s Station around midnight. The Confederate pursuit was slow not reaching Baldwin until the 22nd. The locomotive of the Union train bearing the Union wounded broke down at Ten Mile Station. The 54th MA used ropes to pull the train 3 miles before horses were brought up to help. It took 42 more hours to get the train back to Jacksonville. The Union suffered 1,861 killed, wounded, and missing. This casualty rate of 34% was one of the greatest losses in terms of percentage of total force in any battle by the Union during the entire Civil War. Confederate casualties totaled 946. A number of Black soldiers left behind on the field were shot and killed by Confederates.

The Olustee Battlefield Historic State Park

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