Marshall's Raid Through Eastern Kentucky, March-April 1863 - On March 15, 1863, Marshall comes through Pound Gap with 1,800 mounted men, including Col. Henry Giltner's 4th Kentucky, Col. Thomas Johnson's 2nd Kentucky, Col. Ezekiel F. Clay's 1st Kentucky, Col. Ben E. Caudill's 11th Kentucky, and a squadron of men under Captain G.M. Jessee. He is later joined by Col. Jack May and his newly-formed 10th Kentucky Cavalry. After dispersing a Union force that has been harassing Col. Roy Cluke's cavalry at Salyersville, Marshall marches to Louisa, intending to capture the Union supply depot at Fort Bishop, but when he and his officers arrive on the scene and discover how well-defended it is, they change their plans. After this fiasco, they move through Breathitt, Wolfe, and Owsley counties, burning and plundering 43 Wolfe County and Owsley County farms before returning to their base in southwestern Virginia.
Skirmish at Smokey Valley, March 24, 1863 -Eighteen hundred Confederate cavalry led by Marshall attack a defensive position held by 300 mounted men of Col. George W. Gallup's 14th Kentucky Mounted Infantry, forcing them to fall back to Fort Bishop. Union losses are one killed, two wounded, and four missing. On the following day, after inspecting the fort's defenses with his telescope, Marshall decides not to attack.
Battle of Turman's Ferry, January 9, 1864 - While camped for the night in a schoolhouse near Turman's Ferry on the Big Sandy River fourteen miles above Catlettsburg, 75 men of the 39th Kentucky Infantry are surrounded and attacked by 150 Confederate cavalry under Colonel M.J. Ferguson. Awakened from their sleep, the Kentuckians flee in panic, running barefoot into the snow and sub-zero weather. Fourteen are killed or wounded in the attack and many others suffer frostbite.
Clay's Raid into Eastern Kentucky, March-April 1864 - Six hundred Confederate cavalry under Colonel Clay come through Pound Gap and march down the Big Sandy to Paintsville, where, on April 13, they encounter four companies of Gallup's 14th Kentucky Mounted Infantry and 500 home guards. When the rebels attack the Union position, they are repulsed, suffering two killed, two wounded, and seven captured. Clay then send Gallup a flag of truce, asking for time to bury his dead and exchange prisoners. Judging Gallup's force to be stronger than his own, Clay retreats to Salyersville.
Battle of Puncheon Creek (Half Mountain), April 14,1864 - Colonel Gallup, leading the 14th Kentucky Mounted Infantry under Lt. Col. Joseph R. Brown and the 39th Kentucky Mounted Infantry under Col. David A. Mims—a total of 800 men—launches a surprise attack on Colonel Clay's 600 Confederate cavalry while they are camped at Half Mountain on the Licking River, six miles above Salyersville. A four-hour engagement ensues, during which Clay is wounded in the eye and captured. Confederate losses are 60 killed and wounded and 60 captured, along with 200 horses, 400 saddles, 300 small arms, and all their tents and equipage. Union losses are one killed and four wonded.
Morgan's Last Kentucky Raid, June 2-12, 1864 - Leading 1,400 cavalry and 800 dismounted men, Brig. Gen. John Hunt Morgan comes through Pound Gap, passes down Troublesome Creek, and raids Mount Sterling, capturing 380 Union soldiers. Brig. Gen. Stephen Burbridge is leading a large Federal force up the Big Sandy Valley, and the purpose of Morgan's raid is to divert Burbridge from his objective, Preston's Saltworks at Saltville, Virginia. At Mount Sterling, Morgan's men steal and plunder, taking $80,000 from the Farmer's Branch Bank.
Battle of Cynthiana, June 12-1864 - After raiding Lexington, where they capture 2,000 horses, Morgan and his men march to Cynthiana, where on June 11, they defeat and capture the town's 400-man Union garrison. On the following day, lacking ammunition for their rifles, they are attacked and routed by Burbridge's troopers, who capture their baggage train and send them fleeing in several directions. On their way back to Virginia, Morgan and some of his men pass through Prestonsburg, where Morgan rests his mount and spends a pleasant hours drinking a glass of water and chatting with local ladies on the porch of the John Graham Johns House.