Williamsburg and the surrounding country, including the Loutre River valley, were home to several Southern guerrillas during the Civil War and also stood as an important eastern gateway along the Boone's Lick Trail into Callaway County and Nine Mile Prairie. Capt. Alvin Cobb of "Cobbstown," whose forearm had been accidentally shot off and replaced by a hook, rode with his brothers Frank and Ike as guerrillas; after the July 17, 1861, fight at Overton Run near Fulton, Cobb and some of his men went to the Whetstone Hills north of Williamsburg, then trailed, rode down, and killed Major Benjamin Sharp and Lt. Anthony Jaeger near Martinsburg after ambushing them as Sharp traveled from Danville toward Mexico, Missouri, to speak and recruit Union soldiers. Cobb also led guerrillas at Mt. Zion Church and at Moore's Mill on July 28, 1862, and was reported to have gone to Indian Territory in 1864 and lived until at least 1885 in California. Guerrilla Joe Cole, known for plumed hats and gaudy dress, preyed on local Unionist Germans until soldiers based at Wellsville killed him at a bordello near Portland on December 1, 1863. Dick, Ike, and Jim Berry, sons of early settler Caleb Berry, all rode with Capt. William T. "Bloody Bill" Anderson and likely were with him at Centralia on September 27, 1864; afterward Dick became a deputy sheriff in Montana, Ike ran liquor businesses in Williamsburg and Montgomery County and a restaurant in Fulton, and Jim joined outlaw Sam Bass as a bank and train robber before being mortally shot in Callaway County and dying on October 15, 1877. Anderson himself was said to have stayed in Williamsburg before his October 14, 1864, burning of Danville and destruction of rail depots at Florence and High Hill during General Sterling Price's expedition, a raid ordered to destroy the North Missouri Railroad; Danville, a Unionist town of almost 1,000 people, was practically erased. Williamsburg, established about 1833 after the earlier settlement of Fruits, became a key stop on the Boone's Lick Trail from St. Charles to the Boone family salt lick west of Columbia, and rough country to the east made it a favored provisioning center for settlers moving west. The original road passed through Williamsburg and across northern Callaway prairie, later routes carried travelers by Old Auxvasse Presbyterian Church or southwest through Moore's Mill, Fulton, Millersburg, and Columbia, and the road was heavily used by troops during the Civil War. During the war Williamsburg was also a place where Confederates and their partisans could find food, shelter, and assistance, and it still retained prewar homes on Main Street. Col. Upton Hays, youngest son of Boone Hays and a grandson of Daniel Boone, was born in Nine Mile Township, grew up in Jackson County, outfitted wagon trains to the West, and as a Confederate recruiting colonel worked with William Clarke Quantrill in June and July 1862 to enlist about 300 soldiers in western Missouri; he distinguished himself at Independence and Lone Jack before being killed at Newtonia on September 12, 1862, after which his widow Margaret and their four children moved to Williamsburg and remained there through the rest of the war with support from friends and relatives.
