Union Forces Commanded by:
Brig. Gen. Alexander Asboth
Confederate Forces Commanded by:
*Killed, Wounded and Captured Conclusion: Union Victory
After receiving rather specific information on the status of Confederate defenses in Northwest Florida, Brig. Gen. Alexander Asboth outlined plans for an extensive raid in a letter to superiors dated September 12:
"... I am to start a cavalry raid in the northwest portion of West Floirda.... My
objective is to capture the isolated rebel cavalry in Washington and Jackson Counties, and to liberate the Union prisoners confined at Marianna, to collect white and colored recruits, and secure as many horses and mules as possible.
Asboth's intelligence regarding Union prisoners at Marianna appears to have been faulty, but the rest of his information was remarkably detailed and generally accurate.
Accordingly, he assembled a strike force of 700 men consisting of 3 battalions from the 2nd Maine Cavalry, one battalion from the 1st Florida U.S. Cavalry and two mounted companies of picked infantrymen from the 82nd and 86th U.S. Colored Troops (79 men total).
With assistance from the steamer Lizzie Davis, this force began crossing Pensacola Bay to Deer Point (present-day Gulf Breeze) on September 16, 1864. Asboth himself crossed over on the morning of the 18th and advanced that same day with a portion of the command to Rodger's Gap on the Narrows of Santa Rosa Sound (near present-day Mary Ester).
Here he waited for for the rest of the command to come up and spent the next day preparing for the inland portion of the raid." The USS Lizzie Davis, a former Confederate blockade runner that had been captured by the U.S. Navy, shadowed the force as it moved east along Santa Rosa Sound. Establishing a temporary camp at Rodger's Gap, Asboth offloaded supplies from the USS Lizzie Davis and prepared to move inland on the morning of September 20.
His original plan, as outlined to superiors on September 12, called for a rapid march inland from Point Washington on Choctawhatchee Bay to Marianna - via Vernon in Washington County - and then back by way of the St. Andrews Bay saltworks. At some point, however, he altered this plan to expand the scope of his movements.
His new plan called for an inland march on September 20 via the old Ridge Road to the cattle ranching areas along the Shoal River. From there, he planned to turn east into the populated areas of Walton and Holmes Counties, before crossing the Choctawhatchee River at Cerrogordo and advancing on Marianna from the northwest. Such a line of march would allow his troops to range over a much larger area and would impact virtually all of Confederate-held Northwest Florida. In addition, an approach on Marianna from the northwest would be unexpected and might prove of strategic value.
Turning inland in the morning, Asboth's men pushed up the old Ridge Road through heavy rain. In fact, it would rain continually for the next several days. The soldiers reached the Shoal River area on the morning of the 22nd, rounding up cattle and taking a few prisoners. No fighting seems to have taken place.
By the night of September 22, Asboth had pushed as far east as the modern city of Defuniak Springs. That railroad town had not yet been established and the area was generally characterized by rolling hills and cattle farms. The raiders camped for the night near Lake Defuniak, learning at some point that a small force of Confederate cavalry was camped - unawares - just a few miles away at Eucheeanna Courthouse.
Getting the jump on the Confederates, Asboth moved out early on the morning of September 23 and covered the 3 miles between his Lake Defuniak campsite and Eucheeanna before sunrise. They quickly located the small Confederate camp and Lt. Col. Andrew Spurling and troopers from the 2nd Maine Cavalry swept in on the unsuspecting Southerners at daybreak.
There were several different accounts of the skirmish, but all agree that it wasn't much of a fight. Asboth reported the capture of 9 prisoners of war, including Lt. Francis Gordon of Company I, 15th Confederate Cavalry and 5 of his men. The other 4 prisoners were members of Capt. Robert Chisolm's (Chisholm's) company of Alabama cavalry, then stationed at Marianna. The Federals also took 6 "political" prisoners at Eucheeanna, but these seem to have been released.
A few of the Confederate cavalrymen managed to escape and concern grew that they might alarm the countryside. Asboth sent Lt. Col. Spurling to find them: "It being feared that they would arouse the country and trouble our progress, Lieut.-Col. Spurling, accompanied by Lieut. Jones of Company D, Sergt. Butler, Company B, Second Maine Cavalry, and ten men, all disguised in rebel uniforms, left the main body for the purpose of securing them. This was dangerous business. If captured in Confederate uniforms, Spurling and his men could expect immediate execution. They went as far north as Geneva, Alabama, and followed the path of the main column until September 28, but never came up with the missing Confederates.
Asboth's men inflicted severe damage on the farms around Eucheeanna. Every usable item was taken or destroyed. Food and livestock was confiscated. Weapons were seized. Wagons and carts were taken. The "Emancipation Proclamation" was also enforced with regard to slaves discovered on local farms by the Union troops. Asboth also ordered the destruction of any boats found on the Choctawhatchee River and then pushed north to Cerrogordo in Holmes County, where he crossed the river on September 25 and began his final advance on Marianna.
Although alerted that a raiding party was active in Walton County, Montgomery and his men at Marianna had no idea that they had crossed the Choctawhatchee.