On May 1-2, 1863, Brig. Gen. John Sappington Marmaduke's four Confederate brigades fought at Chalk Bluff while retreating from his second Missouri expedition, usually called the Cape Girardeau Raid, and escaped across the St. Francis River into Arkansas under pursuit by Union troops led by Gen. John McNeil. After failing to take the well-defended Federal supply depot at Cape Girardeau and withdrawing through Jackson and Bloomfield, Marmaduke's force endured nearly constant skirmishing, heavy rain, muddy roads, and high water, destroying bridges on the Whitewater and Castor rivers as they retreated south toward Chalk Bluff. Union forces under Brig. Gen. William Vandever occupied Bloomfield after the Confederates had withdrawn, and on May 1 McNeil's men skirmished with the Confederate rear guard through Four Mile before attacking a strong position at Gravel Hill, where Marmaduke's men, concealed behind crude log-and-brush breastworks, repulsed the 3rd Missouri Cavalry Regiment until Union artillery and reinforcements came up, with little accomplished before dark. Marmaduke had already sent Maj. Robert Smith and a detail of unarmed men ahead on April 30 to build a makeshift bridge and a log raft over the flooded St. Francis at Chalk Bluff, assisted by Gen. M. Jeff Thompson. During the night of May 1, the Confederates crossed one brigade at a time on the fragile bridge, while horses swam the river and Thompson disassembled the artillery and ferried it across on the raft. By daylight on May 2, nearly all of Marmaduke's command had crossed without the Federals realizing it, and the Confederates then cast off the bridge and raft. Later that morning, when McNeil's brigades approached the river, Confederate fire from the Arkansas shore unhorsed McNeil and his aide and inflicted several casualties, while Union artillery answered with an ineffective cannonade before the Confederates marched away. Casualties were probably low, with Vandever estimating Union losses at no more than 50 killed, wounded, and missing. Chalk Bluff gave Marmaduke a tactical victory by saving his command from a major engagement against the river, but his raid failed strategically because he could not hold Missouri, gained only enough recruits to replace losses, left his men poorly armed and fed, and did not divert Federal operations into northern Arkansas.
