Route of Advance. In Aug. 1862, Confederate Gen. E. Kirby Smith left Knoxville to invade Ky. in a planned effort with Gen. Braxton Bragg, who advanced from near Nashville. Smith bypassed Union troops at Cumberland Gap and followed the Old State Road toward Richmond, where U.S. forces opposed his advance. The Old State Road was the major transportation route for Kirby Smith’s army. Over. (Reverse) Moving up the Old State Road, the Confederates skirmished with Union troops on Aug. 29. The next day, Kirby Smith drove Brig. Gen. Mahlon Manson’s Union force back toward Richmond. Kirby Smith’s attack followed the Old State Road for the entire battle, which was a decisive Confederate victory. After the fight, the road continued to be a major thoroughfare.