While the debate over Kentucky's neutrality raged in Frankfort, men of the Big Sandy Region were taking action. For Jack May, Hiram Hawkins, John S. Williams, and others, the choice had already been made. President Lincoln's call for 75,000 volunteers to "put down the rebellion" and the legislative elections of August, 1861, which installed a Unionist majority in Frankfort, were all that was needed for local secessionists to flock to the Samuel May House in Prestonsburg and enlist in the Confederate Army.
This pre-Confederate activity caused genuine concern at the newly established Union headquarters in Louisville. Colonel John Williams' plan may have been to use Prestonsburg as a staging point for a Confederate advance into Central Kentucky. By mid-October, he was in command of all the Confederate troops in the region and was drilling 1,000 soldiers at his camp north of Prestonsburg. However, the region's roads were so poor that it was impossible for the Confederate government to provide him with arms and ammunition.
This, coupled with a lack of support from Confederate forces based in Southwestern Virginia, made any attempt to launch an offensive from Prestonsburg virtually impossible.
Following the engagement at Ivy Mountain, Williams retreated southward from Pikeville and established a camp at Pound Gap. Meanwhile, General Humphrey Marshall was placed in command of all Confederate troops in Southwestern Virginia and ordered to proceed to Prestonsburg "for the protection and defense of that frontier." On November 26th he left his base at Wytheville and marched to Pound Gap with two infantry regiments, a regiment of cavalry, and a battery of artillery. By this time Union General "Bull" Nelson had evacuated his troops from the region, reasoning that his foe's lack of supplies and the lateness of the season made a Confederate counter-attack unlikely.
Marshall reached Pound Gap on November 28th, and, after issuing rifles and uniforms to Williams' command, began advancing into Eastern Kentucky. By December 22nd his Virginia regiments and several companies of the 5th Kentucky were camped three miles south of Paintsville on the farm of Daniel Hager. While Marshall's army was moving down the Big Sandy, a large Federal force under Colonel James A. Garfield was moving up the valley. The first skirmish between the two armies occurred at Tom's Creek, two miles below Paintsville, on January 4, 1862. Thus the stage was set for the decisive Battle of Middle Creek, which occurred six days later.
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