On October 11, 1863, the Third Battle of Boonville was fought from the Boonville wharf as Confederate General Joseph O. Shelby approached from the south after burning a railroad bridge near Otterville. Union sympathizers fled across the Missouri River to Howard County while Boonville prepared for his arrival. Shelby entered town, took much needed supplies, and his troops killed or wounded no one, but they stripped stores of merchandise and plundered more than $100,000 worth of goods in a single day, leaving receipts at Gmelich Jewelry for watches taken by force of arms. As this was happening, about 250 Union troops under Major Reeves Leonard tried to cross the Missouri from Howard County, but turned back when warned that Confederates filled the town, after which Shelby's men opened fire and brought up artillery. At the same time, Colonel Thomas T. Crittenden, coming upriver on the steamboat Isabella with about 100 men, disembarked in Howard County and did not come to the Boonville wharf after learning what had happened. Shelby camped west of Boonville that night and retreated westward the next day, and on October 12 Crittenden and Leonard entered town after the Confederates had left. The wharf itself had long been strategically important: steamboat passengers and merchandise unloaded there and moved up the cobblestone street to town, Confederates guarded it at the start of the Civil War in June 1861, Nathaniel Lyon landed east of Boonville at Merna and approached by back roads in the First Battle of Boonville, and Federal troops remained there during the war before railroads reduced the wharf's economic importance afterward. The site is also tied to Sue M. Bryant, a Boonville Female Seminary student whose red and white graduation dress led to her arrest in Marshall on August 6, 1862, imprisonment in St. Louis after refusing at first to sign an oath of allegiance, and eventual return home in October, and to later wartime changes in Boonville, when recruiting of male slaves as soldiers began there about two months after this battle.