The Battle of Ivy Mountain

The Battle of Ivy Mountain. November 8, 1861. 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. The camp was located in the big meadow below the Samuel May House, the Confederate recruiting station and birthplace of Captain Andrew Jackson May. With the approach of Nelson’s forces, Colonel John S. Williams, whose Confederate recruits were ill-equipped and low on ammunition, abandoned Prestonsburg and fell back to Pikeville. Planning to turn or cut the rebels off, Nelson divided his forces at Prestonsburg and sent one detachment under Colonel Joshua Sill up John’s Creek while he led the main column up the Big Sandy River. As the Union columns converged on his new position at Pikeville, Colonel Williams ordered a large detachment under Captain May to delay Nelson’s advance. May’s men took up position at this point. Waiting in ambush above what was then a narrow bend in the road, May’s Confederates surprised the Federals with a heavy volley but were driven from the heights by superior numbers. May retired toward Pikeville, felling trees and burning bridges to further delay 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 first major clash in Eastern Kentucky, the Battle of Ivy Mountain, ended the first phase of the struggle for the Big Sandy Valley.