In the fall of 1861, General William “Bull” Nelson, Union commander in northeastern Kentucky, was ordered to break up a large Confederate recruiting camp at Prestonsburg, located in the big meadow below the Samuel May House, the Confederate recruiting station and birthplace of Captain Andrew Jackson May. As Nelson’s forces approached, Colonel John S. Williams, whose Confederate recruits were ill-equipped and low on ammunition, abandoned Prestonsburg and fell back to Pikeville. Hoping to turn or cut off the Confederates, Nelson divided his forces at Prestonsburg, sending one detachment under Colonel Joshua Sill up John’s Creek while leading the main column up the Big Sandy River. As the Union columns converged on Pikeville, Williams ordered a large detachment under Captain May to delay Nelson’s advance. May’s men took position here, ambushing the Federals above what was then a narrow bend in the road with a heavy volley, but superior numbers drove them from the heights. May then retired toward Pikeville, felling trees and burning bridges to slow Nelson’s pursuit. After fighting a rear guard action against Sill’s column at Pikeville on November 9th, Williams withdrew back to the Virginia line. The Battle of Ivy Mountain, the first major clash in eastern Kentucky, ended the first phase of the struggle for the Big Sandy Valley.