September 27, 1864, marked one of the bloodiest guerilla conflicts in Missouri throughout the war. It was on this date in Centralia, Missouri 400 bushwhackers led by William "Bloody Bill" Anderson killed all but 32 out of 155 new Union recruits. Despite guerilla insistence that they were attacked first, the brutality of the battle has led this event to be called the "Centralia Massacre." Historically, this event has largely overshadowed the bloodiest day of the Civil War for the Concordia community.
On October 10, 1864, the Bushwhackers, led by William Quantrill were moving west near Freedom Township following the Centralia Massacre headed to Kansas. A group of these Bushwhackers, under the leadership of George Todd and David Poole, were spotted and an alarm was raised by a series of cattle horns. Most of the members of this "home guard" militia mustered at St. Paul's church, but a small group headed straight out toward the Bushwhackers and hid in the brush on the side of the road. The place they set their ambush was about three miles east of the German settlement.
The militia fired a few shots toward the Bushwhackers which gave away their position. The Bushwhackers surrounded the militia as they attempted to flee. All were killed except Henry Dedeke who managed to kill a bushwhacker and hide until the rest left.
The remainder of the home guard was riding out to meet the Bushwhackers but, upon seeing how outnumbered they were, turned to retreat. Still, several were captured and killed. At the end of the day, 26 men of the Concordia community were dead.
On the 150th Anniversary of the event, October 10, 2014, community members dedicated a monument to those killed at the site of the massacre. It sits just north of Holy Cross Lutheran Church in Emma.