The Union destruction against Confederates and militia defending the town of Marianna was the culmination of a substantial Federal cavalry raid into northwestern Florida.

Marianna, the home of Florida's ardent secessionist Civil War governor, John Milton, was an important supply depot and recruiting/mustering center for Confederate militia and reserves.

Gen. Alexander Asboth set out from Fort Barrancas near the Federal-occupied city of Pensacola and rode eastward on a raid through northwest Florida.

The thinly spread local Florida cavalry was unable to provide adequate warning of the size, location, and approach of the raiders.

This left regional Confederate commander Col. Alexander B. Montgomery guessing as to the Federal objective and strength, leading to critical delays in calling up reserves and telegraphing for assistance in containing the raiders.

To disguise his intentions, Asboth had a detachment destroy Douglas' Ferry on the Choctawhatchee River, closing passage along the direct road to Marianna.

Campbellton was a crossroads, so the Federals could still move into Georgia or Alabama, into the richest agricultural region in northwest Florida or back southeast toward Marianna.

In attempting to picket each potential route of advance with his small force, Montgomery was unable to draw his meager reserves together in strong defense of any of them.

Montgomery's cavalry contested the crossing of Hopkins' Branch, 3 miles (4.8 km) from Marianna with the intention of falling back into town via an old bypass (now Kelson Avenue) rather than the main road.

Many of the Rebel troopers were able to push their way past the Union flanking force and escape, but many homeguards, conscripts, and militia were pinned in town.

In town, the remaining defenders on the south side of the street broke and ran, but those near the church stubbornly held out as the detachment of U.S.

Due to the fiercer-than-expected fighting and high casualties, particularly among the officers, Asboth's plan to turn south toward St. Andrews Bay was cancelled.