Battle of Olustee The Battle of Olustee or Battle of Ocean Pond was fought in Baker County , Florida on February 20 , 1864 , during the American Civil War . It was the largest battle fought in Florida during the war . Background . In February 1864 , Major General Quincy A . Gillmore , commander of the Union ' s Department of the South at Hilton Head , South Carolina , ordered an expedition into Florida to secure Union enclaves , sever Confederate supply routes ( especially for beef and salt ) , and recruit black soldiers . Brigadier General Truman Seymour , in command of the expedition , landed troops at Jacksonville , in an area already seized by the Union in March 1862 . Seymour ' s forces then made several raids into northeast and north - central Florida . During these raids he met little resistance , seized several Confederate camps , captured small bands of troops and artillery pieces , liberated slaves , etc . However , Seymour was under orders from Gillmore not to advance deep into the state . Seymour ' s preparations at Hilton Head had concerned the Confederate command in the key port city of Charleston , South Carolina . General P . G . T . Beauregard , correctly guessing Seymour ' s objective was Florida , felt these Union actions posed enough of a threat for him to detach reinforcements under Georgian Alfred H . Colquitt to bolster Florida ' s defenses and stop Seymour . Colquitt arrived in time to reinforce Florida troops under the command of Brigadier General Joseph Finegan . As Colquitt ' s troops began arriving , Seymour , without Gillmore ' s knowledge , began a new drive across north Florida with the capture of Tallahassee as a possible objective . Battle . Following the Florida , Atlantic and Gulf Central Railroad , Seymour led his 5 , 500 men in the direction of Lake City . At approximately 2 : 30 in the afternoon of February 20 , the Union force approached General Finegan ' s 5 , 000 Confederates entrenched near Olustee Station . Finegan sent out an infantry brigade to meet Seymour ' s advance units and lure them into the Confederate entrenchments , but this plan went awry . The opposing forces met at Ocean Pond and the battle began . Seymour made the mistake of assuming that he was once again facing Florida militia units that he had previously routed with ease and committed his troops piecemeal into the battle . Finegan and Seymour both reinforced their engaged units during the afternoon and the battle took place in open pine woods . The Union forces attacked but were savagely repulsed by withering barrages of rifle and cannon fire . The battle raged throughout the afternoon until , as Finegan committed the last of his reserves , the Union line broke and began to retreat . Finegan did not exploit the retreat , allowing most of the fleeing Union forces to reach Jacksonville . However , the Confederates did make a final attempt to engage the rear element of Seymour ' s forces just before nightfall , but they were repulsed by elements of the 54th Massachusetts Volunteer Infantry and the 35th United States Colored Troops , both composed of African - American soldiers . The Confederate cavalry commander received criticism for failing to pursue the retreating Union forces . Aftermath . Union casualties were 203 killed , 1 , 152 wounded , and 506 missing , a total of 1 , 861 men — about 34 percent . Confederate losses were lower : 93 killed , 847 wounded , and 6 missing , a total of 946 casualties in all — but still about 19 percent . Union forces also lost six artillery pieces and 39 horses that were captured . The ratio of Union casualties to the number of troops involved made this the second bloodiest battle of the War for the Union , with 265 casualties per 1 , 000 troops . Soldiers on both sides were veterans of the great battles in the eastern and western theaters of war , but many of them remarked in letters and diaries that they had never experienced such terrible fighting . The Union losses caused Northern authorities to question the necessity of further Union involvement in the militarily insignificant state of Florida . There is evidence from Confederate memoirs and letters that Confederate troops murdered wounded and captured African - American Union soldiers . On the morning of 22 February , as the Union forces were still retreating to Jacksonville , the 54th Massachusetts was ordered to counter - march back to Ten - Mile Station . The locomotive of a train carrying wounded Union soldiers had broken down and the wounded were in danger of capture . When the 54th Massachusetts arrived , the men attached ropes to the engine and cars and manually pulled the train approximately three miles to Camp Finegan , where horses were secured to help pull the train . After that , the train was pulled by both men and horses to Jacksonville for a total distance of ten miles . It took forty - two hours to pull the train that distance . In the South , the battle was seen as a spirit - raising rout . One Georgia newspaper referred to Union forces as walking " forty miles over the most barren land of the South , frightening the salamanders and the gophers , and getting a terrible thrashing . . . " Today , the battlefield is commemorated by the Olustee Battlefield Historic State Park , a part of the Florida State Park system . This park is located within the Osceola National Forest , on U . S . 90 . The actual battlefield consists of the state park , part of the national forest and privately held land on the south side of U . S . 90 . There is an annual historical reenactment that takes place on the site of the battle , and nearby Lake City ( in Columbia County ) has hosted the yearly Olustee Battle Festival , a separate event , since 1976 . On one weekend every February ( see Citations ) , thousands of reenactors from across the U . S . , and even from overseas , come to the Park to reenact the Battle of Olustee . Reenactors begin arriving as early as Thursday to set up . Friday is " School Day " as thousands of students arrive to spend the day watching demonstrations and listening to living historians discuss various aspects of the war and life in the United States during the 1860s . The public is invited to attend the event on Friday , Saturday and Sunday , visit the camps , view demonstrations , interact with living historians , shop at numerous sutler tents for Civil War merchandise , and attend the battle on each day . A large selection of modern day food is available from Friday through Sunday inside the park . The reenactment of the Battle of Olustee is co - sponsored by four organizations : the Olustee Battlefield Historic State Park Citizens Support Organization ; the Florida Department of Environmental Protection - Recreation and Parks ; the USDA Forest Service - Osceola National Forest ; and The Blue - Grey Army , Inc . Battle lithograph . The lithograph at the top of the page was printed by the firm of Kurz and Allison in 1894 . It depicts soldiers of the 8th U . S . Colored Troops advancing against Confederate entrenchments . While frequently used in media about the Battle of Olustee , it is inaccurate as the artist knew little about the battle . The Confederates troops during the battle were well in advance of their prepared positions , and neither side fought from behind fortifications , as the battle took place in a pine forest ( see map - top of map is approximately due West ) . Plus , there were very few large cleared areas ( as also shown incorrectly in the lithograph ) . The dotted red line on the map indicates the location of the Confederate trenches . The annual reenactment begins in a pine forest so that reenactors can experience fighting as the soldiers did in 1864 . However , the fighting then moves into a large , cleared area so that spectators also can view the battle .