Dickison is mostly remembered as being the person who led the attack which resulted in the capture of the Union warship USS Columbine in the "Battle of Horse Landing".

This was one of the few instances in which a Union warship was captured by land-based Confederate forces during the Civil War and the only known incident in U.S. history where a cavalry unit sank an enemy gunboat.

[2] On December 12, 1861, Dickison was asked by the Confederate southern commanders if he would join them in their quest upon the outbreak of the American Civil War and he accepted.

He was commissioned a Lieutenant under Captain John M. Martin and served in the Marion Light Artillery in Fort Clinch.

Dickison had returned from a successful raid and received the following recognition from Major General Sam Jones, his Commanding officer:[2][3] I directed Captain Dickison, of the 2nd Florida Cavalry, who had just returned from a most successful raid east of the Saint John's, to endeavor to get in the rear, and concentrated on a large a force as I could at Newnansville.

Captain Dickison reports that he killed and wounded between sixty and seventy, and captured a few, with very slight loss on his part.

On May 21, 1864, Lola Sánchez overheard three Union officers discuss the plans that their unit had for a raid against the Confederate forces.

The plan was to go into effect the next morning and consisted of a surprise attack on the Confederates while they slept with the aim of proceeding towards St. Augustine to "liberate" supplies for the Union Army.

[4][5] She decided that it was of utmost importance to notify Captain Dickison at Camp Davis, just a mile and a half from her home.

After the meeting she returned home, the whole event took an hour and a half, and her absence went unnoticed by the Union soldiers in her residence.

The Confederate forces had placed artillery guns on the banks of the river and opened fire on the approaching Union gunboats.

This was one of the few instances in which a Union warship was captured by land-based Confederate forces during the Civil War and the only known incident in US history where a cavalry unit sank an enemy gunboat.

[2] On August 17, 1864, Dickison was told that members of the Union Army had arrived at the town of Starke and that they had burned Confederate train cars.

[2][10][11][12] The remaining Union forces in the north central Florida area withdrew to the garrisons at Jacksonville and St. Augustine.

[17] There is also a marker in Waldo, Florida, where Camp Baker was located and where Dickison and his men bivouacked during the closing weeks of the conflict.