The Battle of Natural Bridge: Tallahassee's Last Stand

By Joe Marzo

Common Questions: When and where did the Battle of Natural Bridge take place? Why was the Natural Bridge crossing so strategically important during the Civil War? Who led the Union and Confederate forces in the battle? What role did the Florida Military and Collegiate Institute cadets play in the fighting? Why is the Battle of Natural Bridge significant in Florida’s Civil War history?

Florida’s Last Stand

By the spring of 1865, the American Civil War was nearing its end. Confederate armies were collapsing across the South, and Union forces had already captured most major ports and rail lines. Yet in one quiet corner of Florida, a small but determined group of soldiers, volunteers, and teenage cadets made a final stand that would enter state legend.

The Battle of Natural Bridge, fought on March 6, 1865, was the last significant Civil War engagement in Florida and one of the few Confederate victories during the war’s final months. It was fought just south of Tallahassee, along the St. Marks River, where a natural limestone bridge spanned the water. Though smaller in scale than battles elsewhere, its outcome ensured that Tallahassee would remain the only Confederate state capital east of the Mississippi not captured by Union forces.

The Road to St. Marks

By early 1865, Union forces controlled much of Florida’s coastline. They had long occupied Jacksonville and parts of the Panhandle, but Tallahassee—Florida’s wartime capital—remained under Confederate control. As Union General William T. Sherman swept through Georgia and into the Carolinas, the Union high command wanted to secure Florida’s interior and finally bring the state to submission.

To achieve this, Union Brigadier General John Newton launched an expedition from Cedar Key and Newport with about 700 men, including troops from the Second and Ninety-ninth U.S. Colored Infantry, the Second Florida Cavalry (Union), and detachments of sailors and marines from the U.S. Navy. Their mission: cross the St. Marks River, capture the port of St. Marks, and advance on Tallahassee from the south.

But Confederate forces had other plans. Brigadier General William Miller, a former regular army officer, commanded the Confederate district of Florida. His forces were small—mostly local militia, home guards, and volunteer units—but they knew the terrain. When Miller learned of the Union landing, he moved quickly to block the crossings over the St. Marks River, including the key point known as Natural Bridge, where the river disappeared underground before resurfacing, leaving a narrow strip of solid ground across it.

The Natural Bridge

The “Natural Bridge” itself was both a geographical oddity and a defensive advantage. It allowed movement across the otherwise swampy, winding St. Marks River without the need for a built bridge—making it the only practical crossing for miles. Whoever held the bridge could control access to Tallahassee.

Confederate forces rushed to fortify the area, building makeshift breastworks along the southern bank. They were joined by men from the Milton Light Artillery, Confederate infantry companies, and most famously, the cadets of the Florida Military and Collegiate Institute—the forerunner of today’s Florida State University. Some of these cadets were barely in their teens, but they would soon find themselves in the thick of battle.

The Union Advance

Before dawn on March 6, Union troops began moving inland from Newport toward Natural Bridge. The terrain was miserable—muddy, heavily wooded, and threaded with swamps. Union attempts to cross at Newport had already failed when Confederate skirmishers destroyed the bridge and held the opposite bank under fire. Now Newton aimed to outflank them by marching upriver to the Natural Bridge crossing.

Guided by locals familiar with the backcountry, the Confederate commander anticipated the move and positioned his men accordingly. When the first Union skirmishers approached Natural Bridge just after sunrise, they were met by a volley of musket and cannon fire.

The Second U.S. Colored Infantry and Ninety-ninth U.S. Colored Infantry fought bravely at the front, pressing through thick smoke and brush in repeated attempts to storm the Confederate line. The Union Navy’s sailors and marines, many armed with only revolvers or short carbines, also joined the fight, but the Confederate position was too strong.

The Fight for the Bridge

The battle raged through the morning. Union troops made several assaults against the Confederate defenses, but the narrow terrain left them little room to maneuver. Every approach across the natural span was swept by concentrated fire. The 1st Florida Cavalry (Union), made up of Floridians who had joined the Union cause, found themselves fighting against neighbors and even former friends entrenched across the river.

The Florida cadets, stationed near the center of the Confederate line, helped man artillery pieces and deliver ammunition. Their composure under fire impressed even hardened veterans. One observer later noted that “they fought with the steadiness of regulars.”

By early afternoon, after several failed attacks and mounting casualties, General Newton realized that further assaults would only lead to slaughter. He ordered a withdrawal back toward the coast. The Confederates, exhausted but elated, held their ground.

Aftermath and Significance

When the smoke cleared, Confederate losses stood at around 26 casualties, while the Union suffered nearly 150 killed, wounded, or missing. The numbers were small by Civil War standards, but the symbolic impact was enormous.

The victory at Natural Bridge kept Tallahassee in Confederate hands until the official surrender in May 1865. It also became a rallying point for Southern pride in the war’s final days. For the Union, it was a frustrating failure—one of the last setbacks suffered in a war that was all but over.

The battle also demonstrated the bravery of the African American soldiers who led many of the Union assaults. Despite being outnumbered and fighting against entrenched positions, the U.S. Colored Troops fought with determination and discipline under heavy fire. Their participation, like at Olustee a year earlier, underscored their vital role in the Union war effort—even in the face of overwhelming odds.

Remembering the Battle

After the war, the site of the battle remained largely rural and undeveloped. Over time, veterans and local citizens began to commemorate the event. In 1919, a small granite monument was erected to honor the Confederate defenders, including the young cadets who had fought there.

Today, the site is preserved as Natural Bridge Battlefield Historic State Park, located about 12 miles south of Tallahassee. Visitors can walk interpretive trails through the pine woods and along the St. Marks River, where historical markers recount the action. Each year, reenactors gather to recreate the battle, complete with artillery demonstrations and living-history displays.

The park also contains a memorial to the Union dead, who for decades went unrecognized in the shadow of Confederate commemoration. Modern preservation efforts have sought to tell both sides of the story—the courage of the defenders and the sacrifice of those who attacked in the name of liberty and Union.

Legacy

The Battle of Natural Bridge may not have changed the course of the Civil War, but its impact on Florida’s history was lasting. It preserved Tallahassee’s distinction as the only Confederate capital east of the Mississippi not taken by Union forces and became a symbol of local resilience.

At the same time, it serves as a reminder of the complexity of the war in Florida—neighbors divided, young cadets sent into battle, and African American soldiers fighting for freedom on southern soil.

More than 160 years later, the pine forests still stand quiet along the St. Marks River. But the story of Natural Bridge endures—a story of courage, tragedy, and a final flicker of defiance at the very end of America’s bloodiest war.

Sources

• Florida Center for Instructional Technology – Battle of Natural Bridge

• American Battlefield Trust – Battle of Natural Bridge

• History.com – This Day in History: Battle of Natural Bridge

• Florida State Parks – Natural Bridge Battlefield Historic State Park