General Marmaduke ordered Colonel Carter's column to advance toward Bloomfield, Missouri and attempt to capture the Federal garrison there under the command of US Brigadier General John McNeil. If McNeil had been able to escape, the Confederates thought that he would head north to Pilot Knob, the Union headquarters of the region. Thus Marmaduke accompanied Colonel Shelby's column north to Fredericktown to intercept such an attempt. Shelby's column arrived at Fredericktown on April 22, 1863, but Carter's column did not reach Bloomfield until April 23 because of difficulty crossing the Mingo swamps. Carter arrived at Bloomfield to find that McNeil had left it in ruins two days earlier. Having learned of Marmaduke's position on the road to Pilot Knob, McNeil disobeyed his orders to retreat to Pilot Knob and instead fled northeast to heavily fortified Cape Girardeau, arriving on the evening of April 24.