Affair at Bailey’s

A brief encounter between a Union scouting party and a band of Confederate guerrillas, this skirmish was one of many used by Federal forces to disrupt enemy efforts in northwestern Arkansas during the Civil War.

Colonel John E. Phelps of the Second Arkansas Cavalry (US) received orders from Brigadier General John Sanborn to move from Cassville, Missouri, into Arkansas in an effort to interrupt Confederate efforts to launch a raid into Missouri. On January 17, 1864, Phelps led two companies of his regiment into Arkansas and arrived at Berryville (Carroll County) the next day, joining three more companies already in the town. Due to a large number of sick and absent men, Phelps remained at Berryville until January 20, when he moved out with all of his healthy men, numbering 166. Other Federal commands were operating in the area to support Phelps’s mission, including a group from the First Arkansas Cavalry (US).

Phelps and his men spent the night about five miles north of Carrollton (Carroll County) and moved about thirty miles to the edge of Rolling Prairie on January 21. During the day’s march (with Company C of the Second Arkansas serving as flankers to ensure that enemy troops did not attack the main column), the Union troops encountered their first enemy resistance. Under the command of Lieutenant William Orr, the Federals surprised a party of guerrillas at the Bailey home located on Crooked Creek. Acting quickly, Orr led his men in an attack against the four enemies, killing two and mortally wounding a third; the fourth apparently escaped. The Federals did not suffer any casualties.

The Federals camped at the edge of Rolling Prairie, and the men were joined by another group from the Second Arkansas, numbering thirty-four, which brought the total number of men under Phelps’s command to 200. Continuing their movement the next day, the Federals experienced more fighting near Tomahawk and continued their search for more enemy units. The Federals remained in the field until February 7, fighting several other small engagements and severely disrupting Confederate preparations in the area by killing numerous enemy combatants and capturing many wagons and other supplies.

The brief engagement at Crooked Creek was typical of the war fought through much of Arkansas. In this war of attrition, the Federals could successfully hold their outposts against Confederate units by keeping them off balance and engaging the enemy wherever they could be found.

For additional information:
The War of the Rebellion: A Compilation of the Official Records of the Union and Confederate Armies. Series 1, Vol. 34, Part I. Washington DC: Government Printing Office, 1889.

David Sesser
Henderson State University