The skirmish was the result of an attempt by Union Brigadier General John Schofield to trap a body of Confederate cavalry reported to be at McGuire's Store.

Brigadier General Samuel R. Curtis' Union victory at the Battle of Pea Ridge on 7–8 March 1862, fought in northwest Arkansas, was a significant strategic success.

In subsequent operations, Curtis' army nearly captured Little Rock and successfully occupied Helena in the eastern part of the state.

Within ten weeks, Hindman created an army of 20,000 Confederate soldiers in Arkansas and kindled guerilla operations against Federal authority in Missouri.

[3] Because Hindman's exactions provoked the influential and wealthy classes to turn against him, President Jefferson Davis appointed Lieutenant General Theophilus H. Holmes to command the department, which was expanded to include Arkansas, Indian Territory, western Louisiana, Missouri, and Texas.

[4] In early September, Hindman led a motley force of 6,000 men from Fort Smith, Arkansas, into southwest Missouri.

Brigadier General Frederick Salomon's brigade bumped into the Confederates and was mauled in the First Battle of Newtonia on 30 September 1862, losing 250 casualties.

A Kansas division under Brigadier General James G. Blunt came from the north and more Union troops under Schofield approached from the east.

On 4 October, Schofield and Blunt began bombarding Newtonia with artillery, causing a panicky flight of the Confederates from the town.

[6] Pleased with his easy success, Schofield asked his superior Curtis, now a major general, for authorization to pursue the Confederates into Arkansas.

[12] Blunt proposed moving south to seize Fort Smith while Schofield wanted his troops to remain where they were to support the local pro-Union citizens.

After finding that Rains had gone on a drunken binge, Hindman sacked him and appointed Brigadier General John S. Marmaduke to lead his cavalry.

Totten and Schofield headed south from Osage Spring toward Fayetteville at dusk on 27 October with 3,000 troops, including infantry, cavalry, and artillery.

The column set out on Telegraph Road, but turned east at Robinson's Crossroads, guided by local pro-Union citizens.

[15][note 2] Herron's horsemen brushed aside Confederate pickets at Oxford Bend on the Middle Fork of the White River about 5 mi (8.0 km) north of McGuire's Store.

One of Hawpe's cavalrymen complained that his regiment was armed with shotguns that, "will hardly stick a ball into butter at the distance of sixty paces".

While the two sides exchanged fire, causing few casualties, Herron dimly began to realize that he was facing east toward Huntsville.

Cravens managed to reform his soldiers in a second position at their camp, 1 mi (1.6 km) to the rear, while asking Marmaduke for assistance.

When the troopers of the 1st Iowa encountered Shelby's brigade deployed across the road to Huntsville, Herron decided it was time to leave and he ordered his troops to march west to Fayetteville.

When Hindman heard the gunfire from the McGuire's Store skirmish, he halted his infantry column and rode to where Marmaduke and Shelby were posted.