On August 11, 1862, the federal government directed that 5,000 soldiers stationed in and near Charleston be brought to Washington, to be used in the more active eastern theater of war. This reduction of federal strength in the Kanawha Valley did not pass unnoticed. On August 18, Confederate Gen. William Wing Loring began planning an attack into the region. Loring sent his cavalry on an extensive sweep through the area north of the Kanawha Valley. Gen. Albert G. Jenkins, a Cabell County native, led the raiding party. He started from Salt Sulphur Springs in Monroe County on August 22, with 550 men.

Jenkins's troopers rode first into the Tygart Valley, skirmishing briefly with U.S. forces near Huttonsville. On August 30, the raiders attacked and occupied Buckhannon, where they captured 20 prisoners, 5,000 stands of small arms, and a vast supply of ordnance, stores and clothing. The following day Jenkins's men occupied Weston. They paroled a few prisoners, destroyed the telegraph office, and rode for Glenville. Remaining briefly at Glenville, the raiders arrived at Spencer on September 2. There they surprised and captured several companies of the 11th West Virginia Infantry. Arriving at Ripley, on September 3, the Confederates found no enemy force and captured the federal paymaster, relieving him of $5,525.

On September 4, Jenkins and his men crossed the Ohio River and became the first to raise the Confederate flag on Ohio soil. The following day they attacked federal forces at and near the Mason County courthouse, then moved into Buffalo, Putnam County. On September 8, Jenkins's raiders rode into Barboursville, skirmished with the enemy, remained there for two days, then rode into Wayne, Logan, and Raleigh counties. The Jenkins raid proved that Union defenses in the Kanawha Valley were inadequate and on September 13, 1862, a larger Confederate force captured Charleston, remaining there until late October.