On the morning of the 5th the Union column, about 900-1000 men, moved out toward the East River bridge with Companies G and H of the 2nd USCT acting as skirmishers. Upon reaching the bridge they saw that Milton and his men had pulled up the planking. During the night Lieutenant Colonel George Scott of the 5th FL Cavalry had arrived with a few of his men and assumed command. He had also brought with him one 12-pounder from Dunham’s Battery commanded by Lieutenant Rambo. Major Lincoln ordered the 2nd USCT forward. For unclear reasons the Confederates did not shell the Union column as they approached the bridge and after a brief fight the Rebels were overrun abandoning their gun after only firing it once without spiking it. The main Union force arrived shortly thereafter at the bridge under General Newton. After repairing it the Federals moved on toward Newport eight miles away. The path each side would take during the expedition is shown below.

Lieutenant Colonel Scott and his men beat the Federals to Newport. There they dismantled the bridge. He left a small force on the east bank of the river, if the Federals decided not to cross they were to shadow them. Scott also ordered buildings on the east bank including the workshop and mill of Daniel Ladd burned to prevent Union soldiers from using them. A small group (35 men) of home guards from Captain James Smith’s company arrived as did 20 seaman from the gunboat Spray and 25 artillerymen from Campbell’s Georgia Seige Artillery. These reinforcements when added to the men Scott brought with him from the East River bridge gave him a force of a little over 100 men. As the Federals approached the town they could see smoke clouds rising in the distance. Newton ordered Major Weeks forward with the 2nd FL to try and save the bridge thinking it had been set on fire but could not advance under heavy fire from the opposite bank. The Confederates had destroyed the bridge at both ends. The Federals next tried to shell the Confederates from their works with two boat howitzers for about an hour but this also failed. Confederate General William Miller reached Newport around 5:00 PM with a company of old men and young cadets from the West Florida Seminary (now Florida State University) and a few Confederate marines from the gunboat Spray. Firing diminished as darkness fell and Newton realized he would not be able to force a crossing at Newport and needed a new plan. Shown below is the view of the St. Marks River from the modern-day bridge at Newport.

General Newton decided to cross eight miles further upstream at Natural Bridge. He left Weeks behind with the 2nd FL Cavalry to prevent the Confederates from repairing the bridge and crossing in his rear. This significantly weakened his force as now he would only lead men from the 2nd and 99th USCT and artillery, a total of less than 600 men. They stopped at Tompkins’ Mill along the way to rest for several hours. On the west bank of the river Confederate scouts under Lieutenant Croom spotted the Federals heading north. In response General Miller ordered Colonel Scott to take three cavalry units who had just arrived and parallel the Union force up the opposite bank. Regional Confederate commander General Samuel Jones now at Newport and General Miller knew the Federals would be headed to Natural Bridge. Natural Bridge was in reality not a bridge but a narrow strip of land where the St. Marks River passed underground through a natural cavern of sink holes. Miller would remain at the bridge for the time being while Jones rode off to begin moving the reinforcements coming into Tallahassee to Natural Bridge. Around midnight General Miller was made aware by Captain Samuel Spencer that the troops at Fort Ward were about to abandon and blow up the fort. The two officers arrived there and found the men in a panic having heard the firing in Newport and seeing Union gunboats advancing up the St. Marks River. Miller assured the men that they were in no danger with the river crossing blocked. He also threatened to try anyone leaving their post as a traitor. While the Union was attempting to cross at Newport and later resting at Tompkins’ Mill train loads of Rebels were arriving in Tallahassee throughout the day on the 5th. Units were sent by rail to Camp Randolph where they offloaded, formed ranks, and were led to Natural Bridge by guides provided by General Jones. The Federals moved out from Tompkins’ Mill at 2:00 AM on the 6th. Lieutenant Colonel Scott and his three cavalry units had no trouble reaching Natural Bridge first given that they were traveling on horseback on the better road. They formed near the crest on the eastern side of the narrow “bridge”. The ground gradually sloped upward from the river to their line. In addition, the ground to the north and south were impassable swamps that hindering any attempt at flanking movements. Scott was not there long when Confederate Colonel James Daniel’s column arrived. He would assume command as the senior officer and positioned the 1st FL militia on the left, the 1st FL Reserves in the center, and Major Milton’s dismounted cavalry on the right. Two guns were positioned to the right of the road. At dawn Major Lincoln with Companies B and G of the 2nd USCT pushed Lieutenant Croom’s scouts across the bridge back to the main line east of the river. There the Federals came under heavy fire from the Confederates and had to withdraw (see map of the battle below). A second attack also failed during which Colonel Daniel was injured when thrown against a tree by his horse.

General Newton explored the possibility of flanking the Confederate line. A site was identified one mile to the south but the Confederates were already guarding it. Newton stationed Lieutenant Mark Wilson there with a detachment of Company A of the 99th USCT there to prevent the Confederates from crossing to his rear. General Jones arrived on the field about this time to assume command. General Jones was an instructor of artillery at West Point and is thought to have played a role in positioning the six Confederate guns in a semicircle creating converging fields of fire pouring canister into the charging Federals. General Miller arrived on the field with the troops from Newport around 8:30 AM. His men were added to the lines and entrenchments were dug. By 11:00 AM a Confederate line was formed with 1000 men and six cannon that would be aligned against a Union force of 500 men and three cannon. From left to right the Confederate line was 1st Florida Militia, a cannon, an earthwork occupied by the corps of cadets, Houstoun’s guns with 80 home guards in their rear, the 1st FL Reserves, three companies of dismounted 5th FL Cavalry with home guards from Leon County. Meanwhile, the Federals constructed a line of earthworks along a field on the west bank of the river manned by three companies of the 99th USCT, two boat howitzers and the 12-pounder captured at the East River bridge. A Union officer felt the Confederates could be flanked on their right. Colonel Benjamin Townsend with Companies A, B, and H of the 2nd USCT would attempt the flanking maneuver while Major Lincoln with Companies E, G, and K of the same regiment would launch a frontal assault. The 99th USCT would exploit any breakthroughs in the line. The flanking attack after some initial success failed when General Miller rallied the troops there and the Federals encountered impassable ground and could not reach the enemy’s breastworks. Colonel Townsend was wounded during the attack. Major Lincoln’s men charged three separate times to no avail and the Major was mortally wounded. Newton withdrew to his earthwork line 300 hundred yards to the rear. It was around this time that 375 men from the 2nd FL Cavalry arrived on the field. A detachment of home guards was sent back to Newport along with a cannon to reoccupy the trenches on the west side of the river there. The Confederates decided to abandon their excellent defensive position and counterattack but fell into a trap. Lieutenant Colonel Scott ordered the 5th FL Cavalry and the 1st FL Reserves forward. They crossed over the bridge and much to their surprise encountered a second well-formed line of infantry in trench lines supported by a cannon and were easily repulsed despite three determined charges. General Newton receiving word that the Union Navy could only advance up the St Mary’s River to a point 1.5 miles below Port Leon and with his ammunition running low decided to retire. Newton failed to inform Lieutenant Wilson’s detachment who was guarding the crossing a mile to the south and they were cut off and captured. During this process four Federals from the 2nd FL Cavalry that were left to guard the bridge at Newport were captured. Two of these men, Corporal Asa Fowler and Private Peter Pelt, were recognized as deserters from the Confederate Army and were hung as deserters. Naval Commander Shufeldt when informed that Newton was retreating back to the lighthouse sent Acting Ensign Whitman and 40 sailors to secure the East River bridge. The Federals crossed and the bridge was destroyed making furthering pursuit of the Union column impossible.

The Federals suffered a total of 148 casualties with 21 killed, 89 wounded and 38 missing. He waited as long as he could before leaving for the three bridge burning raiding parties to return. Two of the three made it back but were unsuccessful. Two of the men Captain William Strickland and a private John R. Brannon were captured and executed as aronists. General Jones with a total force of between 500-700 men reported 25 Confederate casualties- three killed and 22 wounded.

The battle is interpreted at the Natural Bridge Battlefield Historic State Park.

Sources

The Battle of Natural Bridge, Florida The Confederate Defense of Tallahassee by Dale Cox

Federal Expedition against Saint Marks Ends at Natural Bridge by Edwin C. Bearss The Florida Historical Quarterly Volume 45, No. 4, pages 369-390.

Florida’s Civil War Years by Keith W. Kohl