Kentucky Union sympathizers had trained recruits at Camp Andrew Johnson, in Barbourville, throughout the summer of 1861. Confederate Brig. Gen. Felix Zollicoffer entered Kentucky in mid-September intending to relieve pressure on Gen. Albert Sidney Johnston and his troops by conducting raids and generally constituting a threat to Union forces and sympathizers in the area.

Brig. Gen. Felix Zollicoffer’s men occupied Cumberland Gap and took position at Cumberland Ford to counter the Unionist activity in the area. Brig. Gen. George H. Thomas sent a detachment under Col. T.T. Garrard to secure the ford on the Rockcastle River, establish a camp at Wildcat Mountain, and obstruct the Wilderness road passing through the area.

Brig. Gen. Morgan approached Cynthiana with 1,200 men, on June 11, 1864, at dawn. Col. Conrad Garis, with the 168th Regiment Ohio Volunteer Infantry and some home guard troops, about 300 men altogether, constituted the Union forces at Cynthiana. Morgan divided his men into three columns, surrounded the town and launched an attack at the covered bridge, driving the Union forces back towards the depot and north along the railroad.

While recruiting in southeast Kentucky, Rebels under Col. John S. Williams ran short of ammunition at Prestonsburg and fell back to Pikeville to replenish their supply. Brig. Gen. William Nelson sent out a detachment from near Louisa under Col. Joshua Sill while he started out from Prestonsburg with a larger force in an attempt to “turn or cut the Rebels off.”