Although Too Late to Change the Civil War, This Rebel Victory Gave Florida a Slice of History

It probably seems easy to downplay Florida’s contributions to the Civil War. After all, the state fielded only about 15,000 soldiers to the Confederate cause—a pale number when compared, for instance, with Virginia’s 155,000 or Tennessee’s 120,000—and no major battles tore apart its fertile soil. Also, because many of its major cities and ports fell to Union occupation early in the war, the extent of Florida’s Rebel activity was limited thereafter essentially to raids and minor skirmishes.

Florida, however, has a significant Civil War bragging right to its name: It was the only state east of the Mississippi River whose capital, Tallahassee, never fell to Union occupation—not until the state was handed over in General Joseph E. Johnston’s surrender in April 1865. That achievement would be sealed thanks to a gutty effort by an amalgamation of cavalry, militia, and military school cadets coming together in the Confederacy’s waning days to defeat a larger, more seasoned Union force.

Whether Florida would join the Confederate States of America in the winter of 1860-61 wasn’t always a certainty. On January 3, 1861, state delegates convened to consider following South Carolina in secession from the Union. Those in opposition, known as “Cooperatists,” made up 36-46 percent of the votes cast on January 3—primarily representatives from the state’s Whig/Republican northwestern panhandle and northeastern coast, areas that had developed differently on a social and economic level from central Florida. Their dissension, though, wasn’t enough to combat the Fire-Eaters. Florida’s declaration of secession came a week later, on January 10, 1861.

Across Florida, from Pensacola to St. Augustine, militia and home-guard units began to recruit citizen-soldiers to defend the state, months before the war’s first shots were fired at Fort Sumter. Although several regiments would be shipped off to fight in Virginia, Tennessee, and Mississippi, plenty remained on the home front. The fortifications at Fernandina, St. Augustine, and Pensacola fell into Union hands in the spring of 1862, leaving only central
Florida between the Suwannee and Choctawhatchee rivers in Confederate control. This Middle District saw comparatively little action in the first few years of the war, and even less was demanded of it despite its rich cattle and salt resources.

That all changed after Vicksburg and Port Hudson fell in the summer of 1863 and Confederate states east of the Mississippi River were severed from Texas’ and Louisiana’s vital beef and salt trade, leaving Florida and Georgia to fill the void. A November 2, 1863, circular issued by Major P.W. White, Florida’s chief commissary officer, implored that all surplus beef supplies in the state be contributed to the Confederate Army. “Our honor as a people demands that we do our duty to [the soldiers],” he wrote. “They must be fed.”

By this time, U.S. officials in Washington, D.C., had escalated efforts to bring Florida back into the fold. That, in particular, stood to benefit Abraham Lincoln’s 1864 presidential campaign, as a large number of Unionists lived there and would certainly provide Lincoln key votes if the state were allowed to rejoin the Union. Clearly, that was part of the motivation for the Union expedition into northeastern Florida in February 1864 that ended in defeat at the Battle of Olustee—a clash that featured two African American regiments: the 35th USCT and the famed 54th Massachusetts.

In early 1865, troops from Cedar Keys, led by Major Edmund S. Weeks of the 2nd Florida Cavalry (U.S.), conducted a raid toward Newnansville with 250 men, including Union sympathizers from Taylor County. To confront the Federal forces, Confederate raiders were sent in by Maj. Gen. Samuel Jones, newly in command of the Department of Florida and South Georgia. On February 13, the raiders clashed at Station 4 along the railroad near Cedar Keys. The conflict lasted several hours, ending in a Union retreat. Confederate Captain John Dickison, known as the “Swamp Fox,” inflicted more than 70 Union casualties and seized a substantial haul of supplies.

A separate attack by Confederates took place at Fort Myers on February 20, led by Major William Footman’s 275-man “Cow Cavalry” and a 12-pounder artillery piece. That Union stronghold on Florida’s peninsula, known to harbor Confederate deserters, was commanded by Captain James Doyle of the 110th New York and garrisoned by 250 soldiers of both the 2nd USCT and 2nd Florida Cavalry (U.S.).

Although the attack on Fort Myers produced no serious casualties or a loss of resources, it was enough—along with the Cedar Keys news—to grab the attention of U.S. authorities.

Federals Move Toward the Capital

Union Brig. Gen. John Newton, named commander of the District of Key West and the Tortugas after the September 1864 fall of Atlanta, felt the Confederate threats needed an immediate response and ordered an expeditionary mission, to be conducted in tandem with vessels from the East Gulf Blockading Squadron.

Confident that neither Fort Myers nor Cedar Keys faced imminent danger of further attacks, Newton set out for St. Marks. His principal goal was to harass the area’s Confederates, destroy necessary war assets, and use Port Leon at the mouth of the St. Marks River to defend against blockade-runners. Depending on how that went, Newton wasn’t ruling out an advance on Tallahassee, 20 or so miles north of St. Marks.

Lieutenant Commander William Gibson led the Union fleet accompanying Newton’s effort, which contained 16 vessels—13 of them steam—and carried a landing force of 900–1,000 troops. Among that force were the 99th USCT, 2nd USCT, and 2nd Florida Cavalry (U.S.).

Formed in Arlington, Va., in 1863, the 2nd USCT joined the Department of the Gulf in early 1864, first seeing duty at Ship Island off the coast of Mississippi. Later transferred to Florida, it participated in several engagements contested between Cedar Keys and Key West, and had helped turn back the recent Confederate attack on Fort Myers.

The 99th USCT, meanwhile, began its Union service as the 5th Corps d’Afrique, an engineering unit formed in New Orleans in the spring of 1864. The regiment found itself relegated mostly to fatigue duty and general labor in Louisiana until it too was sent to Florida. During Maj. Gen. Nathaniel Banks’ Red River Campaign retreat in April 1864, the 99th had experienced heavy Confederate fire while in a non-combat role.

Newton’s plan called for troops to make a night landing on Lighthouse Island on March 3, and to take possession of the nearby bridge spanning the East River, just southeast of St. Marks. Other elements of the landing party were to disembark the following morning and advance on Newport, to the northeast. After securing Newport—destroying in the process any public establishments that could be used to aid the Confederates—those troops were to advance on St. Marks.

Destruction of railroads connecting St. Marks and Tallahassee, as well as any bridges that could facilitate enemy troop movement to and from the capital, was critical to Union success. Gibson’s fleet was to do its part by silencing any coastal artillery, and a trio of vessels was to be sent upriver to threaten Port Leon directly and land a large support force to prevent enemy interference on the road linking St. Marks and Newport.

The Federal fleet arrived late on the 3rd. Because of strong gales and an impassable bar, a party of only 30 seamen of the schooner USS O.H. Lee could deploy to meet a larger party—90 men—under Major Weeks on the East River. At the East River Bridge, the Federal force scared off a small band of pickets, but soon encountered roughly 45 Confederate cavalrymen, who chased Weeks back to the lighthouse.

While attempting to land troops, the Union vessels Honduras and Spirea ran aground on the hidden bars around Lighthouse Island. Three more ships anchored and deployed troops, who on March 4 advanced a couple of miles inland to await for their artillery and supplies to land. Newton and his men waited until the following morning before setting off in the direction of the East River Bridge. They found it partly dismantled, the planks pulled up by the Confederates, who were now well aware of the Federal presence in the area. They would also encounter elements of the 5th Florida Cavalry, commanded by Lt. Col. George Washington Scott, defending the bridge from across the river. 

The dismounted Confederate cavalry, however, were surprised by the 2nd USCT, forcing an outnumbered Scott to fall back and allowing the Federals to repair the bridge and also capture an abandoned artillery piece and several horses before moving north toward Newport with a force of about 900 men.

Baptism by Fire

Weeks’ March 3 assault on the East River Bridge had greatly alarmed authorities in Tallahassee, who began preparing for a Union onslaught. Should St. Marks fall, they knew, the Confederate capital was in immediate danger.

A factor in the Confederate panic was an inflated estimate of the Union force bearing down on Newport—believed to be 1,500–2,000 troops, although only about half that number were actually present. To deter the Federal advance, the bridge at Newport was burned, and detachments of guards were set up at defensible points between St. Marks and Tallahassee.

A call for more troops was sent out. The batch scrounged together, however, would not bolster confidence in Confederate success. As The Tallahassee Floridian Journal reported: “The Militia were ordered out and a unanimous and invincible response was made to the call. Every man and boy capable of bearing arms was at his post. Never, since the first commencement of the war, have the people exhibited a greater spirit.”

Florida Governor John Milton determined that the threat also called for the young cadets at Tallahassee’s West Florida Seminary College to join the fray—all boys under the age of 17 who had been training for future military service. The seminary was founded in the mid-1850s as a place of higher learning for young men west of the Suwannee River, but as the sectional crisis escalated, the institute began incorporating military courses into its curriculum. Alumni of the Virginia Military Institute were brought in to manage this new aspect of learning, and after war broke out, the seminary made the military program its primary focus.

Enrollment spiked just before the war before tapering off as boys left to fight in various theaters. Captain Valentine Mason Johnson, a VMI alumnus and Confederate Army veteran, was appointed principal in 1864. Behind Johnson’s lead, the seminary’s revised curriculum intensified. Informally, it came to be called the Florida
Military Institute.

Many cadets had seen action the previous year when Federal forces advanced toward Olustee and nearby Lake City, Fla. Recalled Cadet William A. Rawls: “All troops, including Home Guards, had been sent to Olustee…all boys big enough to be allowed to go joined them, and went as part of their organization. Many of the Cadets went with them.”

The cadets, Rawls noted, “were [to be] called upon at any time they were needed to perform military duty.” That would be the case in March 1865. Now under Captain Johnson’s command, the youngsters “shouldered their muskets like veterans, and followed with a confidence of inexperience.”

Although the information available to us today varies, it is generally accepted that 34 cadets were enrolled at the school in February 1865. Fewer were involved in defending Tallahassee, however, as many cadets purportedly had to stay behind, not allowed “to go without a written permit from their parents.” Roughly 25 cadets, ages 11–17, would join Lt. Col. Scott’s 5th Florida Cavalry Battalion in the coming engagement.

As they approached Newport, the Federals noticed curling smoke in the distance. Newton sent Weeks and the 2nd Florida Cavalry (U.S.) ahead to investigate, confirming that the city’s bridge over the St. Marks River had been set ablaze by the Confederates. The force under Scott, which included Captain H.A. Gray and the Florida Seminary cadets, had dug rifle pits on the western side of the river, allowing them to enfilade both the river and what remained of the bridge.

In the ensuing three-hour skirmish, the cadets finally received their baptism of fire. Scott’s motley crew stood tall, not budging even in the face of intense artillery fire from two Federal howitzers.

Accountability for several burning buildings in Newport varied depending on the source. The structures, including an iron foundry and a grist mill, had been set aflame either by the Federal aggressors, as a defensive measure by the Confederates, or by embers swept ahead by strong seasonal winds. Nevertheless, Newton determined that crossing the river at Newport was now impractical and decided to divert his army to the north, following an old and unfrequented road about eight miles to a site known as Natural Bridge.

The Confederates would be unable to burn this bridge because, as the name signified, it was a naturally formed strip of land spanning a marshy portion of the St. Marks River. Leaving Weeks and the 2nd Florida Cavalry opposite Newport, Newton redeployed toward Natural Bridge with the rest of his force the night of March 5.

Confederate Brig. Gen. William Miller astutely anticipated Newton’s move, though, and instructed Scott to redeploy a force to the west side of Natural Bridge to prevent a Federal crossing. As more militia and artillery units from Tallahassee became available, Confederate commander Sam Jones rushed them along the Old Plank Road to Scott’s assistance.

Reaching Natural Bridge ahead of the Federal forces, Scott and militia under Colonel J.J. Daniels began to form light breastworks in a semi-circle around the bridgehead, with their flanks anchored on the swampy ground to provide a solid defense.

A total of six artillery pieces, operated by a hodgepodge of units that had responded to the call for troops, were positioned along the line to direct converging fire on any Federal force that attempted to cross. Scott’s cavalrymen dismounted and extended to the right, while reserves and militia bridged the gaps between artillery posts with a line of skirmishers on the east side of the bridge. By the height of the battle, a Confederate force numbering anywhere from 600–700 was engaged with Newton’s force of roughly 900.

At 4 a.m. March 6, Major Benjamin C. Lincoln clashed with Confederate pickets while attempting to cross Natural Bridge with Companies B and G of the 2nd USCT. The “sloughs, ponds, marshes, and thickets” proved a major hindrance to the USCT advance, and though the pickets were driven across the bridge, Confederates on the other side checked the Federal push. An intense firefight ensued as artillery and musket fire from both sides thundered through the backwoods of Leon County.

The cadets, still at Newport, had been ordered to reinforce the new Confederate position earlier that morning and could hear the battle in the distance. As they drew closer to Natural Bridge, they could see the tops of pine trees severed by Federal artillery fire as well as the body of a killed Confederate. After arriving, they were positioned near the center of the line, just left of Captain Patrick Houstoun’s artillery pieces—told “not to fire a gun unless there was a charge made on the battery.”

As cadet Charles Beard recalled, he and his comrades “were lined up with the troops already there, & at once went to work throwing up some kind of breastwork. We polished our bayonets beautifully in the soft sand, and soon had each man a hole and a small pile of dirt in front of it.”

Once entrenched, they had “nothing to do but sit there and wait,” Beard wrote, adding that they “amused ourselves watching the bark fly from the pine trees and twigs fall from bushes around us, and shake the sand that rifle balls would knock on us, from our breastworks.”

Newton ordered his USCT units to charge, though they were repeatedly foiled by Confederate artillery fire. It became clear that although the Federals were not outmanned, they were outgunned. Regardless, the African American soldiers’ tireless determination to carry the enemy position was impressive.

James Dancy, a young artillerist near the center of the line, later described just how hot the fight had been, writing, “If I had put my hat out (but I did not wear one) I could have caught a hatful of bullets.” Cadet Byrd Coles admitted that “no doubt many of the cadets would have been struck if our teachers had not watched us constantly and made us keep behind cover.”

Other attack options were considered, among them a spot for a possible flanking maneuver 1 mile north That was deemed impractical, however, likely because of the difficult terrain.

Advised that a flanking maneuver on the enemy’s right was viable, Newton was unaware that Colonel Caraway Smith’s 2nd Florida Cavalry (C.S.) had arrived that afternoon from Newport to reinforce the Confederate position. Newton ordered Colonel B.R. Townsend and Companies A, B, and H of the 2nd USCT to make another attempt at turning the Rebel flank across the bridge. Meanwhile, Major Lincoln and 2nd USCT Companies E, G, and K would team with Lt. Col. Uri B. Pearsall’s unit from the 99th USCT to provide support.

Despite another valiant effort, the artillery fire was too heavy; Townsend’s men were unable to establish a solid formation on the other side of the bridge. They finally withdrew about 300 yards to regroup, but the 2nd Florida Cavalry (C.S.) misinterpreted the withdraw as a full retreat. Captain H.K. Simmons ordered a charge that was repulsed. Simmons, in fact, was killed in the process, with rumors circulating long afterward it had been friendly fire—that he had been shot in the back by his own men.

Now, Newton had no doubt Natural Bridge was too strongly defended and ordered a retreat to Lighthouse Island and the security provided by the Union fleet. The retreat began about sunset, and the Federal dead and wounded pitifully were left where they lay on the battlefield. Although they would be hampered by felled trees, Scott’s cavalry eagerly pursued the fleeing Federals for a while.

At 4 a.m. the next day, Newton’s Federals arrived back to relative safety at Apalachee Bay. The Union general was quick to blame the setback on a lack of cooperation from the Navy, complaining especially about Gibson’s failure to land a force of seamen at Port Leon and block the road to Newport, as originally planned.

He offered some praise to his officers and men, however, saying “[they] behaved nobly under the most trying circumstances.”

Newton also attributed the mission’s failure on unreliable local intelligence, potential betrayal on the part of his informants, the enemy’s misreported strength of 1,500–2,000 men, and a false assumption that Confederate raids in Pensacola or farther south would draw forces away from St. Marks and Tallahassee. He also wrote that he believed the position at Natural Bridge was “impregnable” and “could have been defended by 200 resolute men and a few pieces of artillery, against five times their number.”

Union casualties were 148 killed, wounded, or missing. The defeated troops were sent back to their regular posts at Cedar Keys, Punta Rassa, and Key West.

Honored as Heroes

The Confederates, who suffered only 26 total casualties, were naturally jubilant in victory. Although the war was nearing its conclusion—a little more than a month left in both the Eastern and Western theaters—the citizens and militia of Tallahassee did not know that. The outnumbered and relatively inexperienced Confederate force at Natural Bridge had triumphed despite the odds. The cadets had played a minor role in the engagement but were welcomed back to Tallahassee as genuine heroes, and were honored with a ceremonial dinner at the state capitol. They would also eventually become Lost Cause icons.

Earning deserved recognition for the Confederate success was Lt. Col. George Washington Scott, who seemed present at nearly every moment of the crisis—from the opening engagement at the East River Bridge to the pursuit of the retreating Federals on March 6. As one newspaper crowed, the victory could be attributed to “the energetic and stubborn resistance of Col. G.W. Scott with his small cavalry force.”

The Confederate soldiers had risen to the occasion, although the hyperbole ascribed to their effort sometimes went too far. As one writer pronounced: “If the people of Georgia had turned out to oppose Sherman as the Floridians have in the battle fought at Natural Bridge, he never could have reached Savannah.”

Victory at Natural Bridge left Tallahassee as the only state capital east of the Mississippi to remain in Confederate hands during the war, relinquished only with General Joseph E. Johnston’s surrender to Sherman at Durham Station, N.C., on April 26, 1865. Union Brig. Gen. Edward McCook finally occupied the city on May 10.

Through the years, Natural Bridge would remain an ever-present memory for Tallahassee’s citizens. Today, through the efforts of the American Battlefield Trust and Florida State Parks, visitors can walk the ground around Natural Bridge where the fighting took place. Remnants of earthworks have been “preserved through neglect” and can be seen among the forested areas around the swamp. Several informative markers tell the story of the battle and a small replica of the breastworks has been recreated. A monument, erected by local descendant associations in 1919, lists the Confederate defenders who helped protect Tallahassee in the twilight hours of the Confederacy.