In the fall of 1864, Confederate Gen. Edmund Kirby Smith ordered Maj. Gen. Sterling Price on a raid into Missouri. Price's goals were to divert Union troops from east of the Mississippi River, gather Confederate recruits, capture or destroy Union war materials and, if at all possible, capture St. Louis or Jefferson City. In what was to be the largest cavalry raid of the war, Price led an army of 12 to 15,000 men into Missouri on Sept. 19.
On Sept. 26, Price attacked Union pickets stationed at the weakly defended Fort Davidson at Pilot Knob. Gen. Thomas Ewing Jr. and 1,450 Union soldiers defended the small hexagonal earthwork fort. Capturing Fort Davidson would provide arms for Price's 3,000 unarmed soldiers and gain a quick victory that would rally sympathizers to his cause.
On the morning of Sept. 27, siege guns of Fort Davidson opened fire as the rebels appeared between Pilot Knob and Shepherd mountains. Price felt that one swift assault would overwhelm the fort. Unfortunately the poorly timed Confederate assaults allowed heavy fire to be directed at each attacking brigade. The Confederates fell back to reorganize and prepare for a renewed attack the next day.
Ewing, low on ammunition, knew his Union forces could not hold out another day. He ordered Fort Davidson evacuated. The soldiers silently crept past Confederate guards at 2:30 a.m. At 3:30 a.m., a small group of soldiers exploded the fort's powder magazine, destroying the remaining supplies. Pilot Knob cost Gen. Price any chance of taking St. Louis or Jefferson City.
The Battle of Pilot Knob battlefield is preserved today as th Battle of Pilot Knob State Historic Site.