The Union takes advantage of Clay County's remotness to escape the seige at Cumberland Gap
USA Brigadier General George W. Morgan
CSA Brigadier General John Hunt Morgan
When, owing to the Battle of Richmond, Colonel Garrard was not able to secure reinforcements for the besieged Union troops at Cumberland Gap (see story), Union General George W. Morgan decided to evacuate the surrounded Gap and follow Garrard's path through Clay County and Manchester to freedom north of the Ohio River. Nearly 10,000 Union soldiers and their supply wagons made their way to Manchester, where on Sept. 19th 1862, they set up camp. They rested for two days before resuming their arduous journey that has come to be known to historians as the "Masterful Retreat."

On their way to Manchester the Union troops were constantly harassed by Confederate toops of the celebrated Rebel raider, John Hunt Morgan. Though it has been widely reported that the two General Morgans were in the county at the same time, the Confederate Morgan was still in Lexington at the precise time the Union Morgan was in Manchester, though John Hunt Morgan's troops were very much present, creating havoc for the Union columns by sniper fire and felled trees.

While in Machester, Private Lewis Stivers, son of Clay County Clerk, George Stivers, got into a fight and killed a fellow soldier. General Morgan decided to make an example of the unruly Stivers and ordered him executed by firing squad. The chilling event took place at the junction of present-day Greenbriar Road and Liberty Hills Road in Manchester.

When they left Manchester, the Union command was again at the mercy of the Rebel command's snipers and tree-fellers. Soldiers suffered terribly in extreme drought conditions, and found no food along the route in Clay County, which by then had already been ravaged by foragers. Eventually George Morgan's men made their way to Charleston West Virginia, where they were later reunited with Colonel T. T. Garrard and his mountainer soldiers, who had been in fighting up to their necks at Richmond and Perryville, and would continue to be at the famous seige of Vicksburg where their commander Garrard was promoted to brigadier general.