Battle of Marianna The Battle of Marianna was a small but significant engagement on September 27 , 1864 , in the panhandle of Florida during the American Civil War . The Union victory over Confederates and militia defending the town of Marianna was the culmination of a substantial Federal cavalry raid into northwestern Florida . Background . Marianna , the home of Florida ' s ardent secessionist Civil War governor , John Milton , was an important supply depot and recruiting / mustering center for Confederate militia and reserves . By late 1864 , it was the largest northwest Florida town still in Confederate hands . A July 1864 raid from St . Andrews revealed the region ' s potential vulnerability to a larger expedition . On September 18 , 1864 , a mounted column of 700 Union troops under Brig . Gen . Alexander Asboth set out from Fort Barrancas near the Federal - occupied city of Pensacola and rode eastward on a raid through northwest Florida . The thinly spread local Florida cavalry was unable to provide adequate warning of the size , location , and approach of the raiders . This left regional Confederate commander Col . Alexander B . Montgomery guessing as to the Federal objective and strength , leading to critical delays in calling up reserves and telegraphing for assistance in containing the raiders . As the raid progressed , the Union cavalry fanned out , destroying or confiscating local foodstuffs and supplies . The Federal troopers captured or scattered a small , mixed company of militia / volunteer Confederate cavalry at Eucheeana on September 23 . To disguise his intentions , Asboth had a detachment destroy Douglas ' Ferry on the Choctawhatchee River , closing passage along the direct road to Marianna . He then proceeded along an alternate route that would take his expedition northwest of Marianna . On September 26 , 1864 , his mounted troopers skirmished with Capt . Alexander Godwin ' s cavalry around Campbellton , only a few miles from Marianna . General Asboth rested his weary men in preparation for a fight at Marianna the next day . Still Colonel Montgomery delayed coalescing his forces and calling out the Marianna homeguard . Campbellton was a crossroads , so the Federals could still move into Georgia or Alabama , or into the richest agricultural region in northwest Florida or back southeast toward Marianna . In attempting to picket all these directions with a small force , Montgomery would be unable to draw his meager reserves together in strong defense of any of them . The battle . On the morning of September 27 , the Federal riders proceeded toward Marianna . When they passed the Old Fort crossroads , Montgomery finally could be certain of their destination . He called out the homeguard and assembled what reserves were already on hand . Montgomery ' s cavalry contested the crossing of Hopkins ' Branch , from Marianna with the intention of falling back into town via an old bypass ( now Kelson Avenue ) rather than the main road . In Marianna , Montgomery deployed the conscripts , militia and homeguard in ambush along the main road ( now West Lafayette street ) . As his skirmishers at Hopkins ' Branch withdrew along the bypass , the homeguard waited behind fences and a crude barricade of wagons and carts . St . Luke ' s Episcopal Church was a few feet away and would play a pivotal role later . Here the plans of both sides ran afoul of one another . Asboth divided his force and led the main contingent on a headlong charge down the main road . Meanwhile , he sent another portion of his force around the bypass along the route Montgomery ' s cavalry had taken . Seeing this and realizing his whole force could be trapped , Montgomery attempted to pull out , but it was too late . The homeguard and militia at the barricades would not budge . Unaware of what awaited him , Asboth ' s wing of the attack rounded the corner straight into a scorching volley by the waiting homeguard . Asboth was wounded in the face and he lost many other senior officers in this volley . Despite being stunned , the Union cavalry rapidly overwhelmed the Confederate cavalry and pushed down the road in pursuit as the flanking force swept in from behind . Many of the Rebel troopers were able to push their way past the Union flanking force and escape , but many homeguards , conscripts , and militia were pinned in town . Colonel Montgomery was captured while attempting to flee to the Chipola River bridge . His escaping cavalry took up positions on the other shore and were able to deter the Union forces from crossing the bridge . In town , the remaining defenders on the south side of the street broke and ran , but those near the church stubbornly held out as the detachment of U . S . Colored Troops engaged them . A dismounted bayonet charge finally forced their surrender . However , several Confederates continued to fire from the church and nearby homes . This led to the church being set ablaze and the defenders shot down as they were smoked out . Casualties . When the fighting ended , some 10 Confederates lay dead or dying , 16 were wounded , 54 were captured and 13 of these were released . Among the wounded was dentist Thaddeus Hentz , a son of famed novelist Caroline Lee Hentz ; he was shot not far from his mother ' s grave . Union casualties were 8 killed or mortally wounded , 19 wounded , and 10 captured . Among the Federal wounded was General Asboth himself . Prior to the war , Asboth had been a hero of the Hungarian Revolution of 1848 and was one of the men who had surveyed Central Park in New York City . His wound would never heal properly , and he would eventually die of its effects in 1868 . Aftermath . Due to the fiercer - than - expected fighting and high casualties , particularly among the officers , Asboth ' s plan to turn south toward St . Andrews Bay was cancelled . Instead , that evening and the next morning , the raiders withdrew toward Choctawhatchee Bay . The column brought with it over 600 liberated slaves , 17 wagons filled with captured arms and stores , 200 captured horses , and 400 head of cattle . At Vernon , the force overran Capt . W . B . Jones ' scout company , taking more prisoners . In all , 96 prisoners from the various engagements would return with the raiders . ( Many of these would die in prison . ) The Confederate forces were too few and too far behind to mount an effective pursuit . It would be decades before the region recovered from the damage inflicted by the raid . Forces engaged . The troops involved in the battle were :