By the late summer of 1862, the Confederacy was looking for ways to reclaim western Virginia. The mountainous counties west of the Alleghenies had voted overwhelmingly Union in the secession crisis and would be admitted as the new state of West Virginia in 1863. Major General William W. Loring, commanding the Department of Southwestern Virginia, planned a coordinated push: he would march north out of the Sulphur Springs country to attack the Kanawha Valley directly, while Jenkins's cavalry would ride a wide arc through the western counties to disrupt Union supply, gather recruits, and make Union commanders look in the wrong direction. The plan worked well enough on paper. Jenkins's force was small - 550 men, mostly mounted infantry rather than regular cavalry - but they were drawn from the region they were riding through, knew the country intimately, and were highly mobile in terrain that hampered larger Federal columns.

Jenkins moved fast. On August 30, his command captured a Union supply depot at Buckhannon and resupplied his poorly armed men. He pushed west into Roane County and captured the town of Spencer on September 2, paroling Union militia prisoners as he went - a courtesy that helped speed the column's progress and reduce the burden of guarding captives. From Spencer he turned northwest toward Ravenswood on the Ohio River. There, on September 4, he forced the river crossing at the so-called Ohio River Ford and rode into Ohio proper. Meigs County and Jackson County had militia but no organized Federal troops in the path of his column. Jenkins's men paroled more prisoners, gathered horses and supplies, and rode through the Ohio countryside for several days before recrossing the river. They were the first Confederate force to occupy Northern soil, weeks before John Hunt Morgan's far more famous Ohio raid of 1863. The strategic effect was limited, but the symbolic effect rippled through both Northern newspapers and Southern propaganda.

While Jenkins was riding through Ohio and back, Loring was marching north toward the Kanawha River. Federal Colonel Joseph A. J. Lightburn, commanding at Gauley Bridge, learned of the threat too late to defend Fayetteville. On September 10, Loring took Fayette Court House. By September 13, Loring had won the Battle of Charleston. Lightburn burned the Elk River bridge and began his eighty-mile retreat down the Kanawha and then north to the Ohio. Jenkins, after recrossing into Virginia, attempted to position his cavalry at Coalsmouth (now St. Albans, at the mouth of the Coal River) to block Lightburn's escape. He was unable to communicate effectively with Loring, and the timing did not quite come together. Lightburn slipped past, took the road north to Ripley, and crossed at Ravenswood - the same ford Jenkins had used a week earlier. The Union army reached Point Pleasant on September 18. The Confederate cavalry, fatigued and out of supply, did not pursue.

In his report of September 20, Loring praised Jenkins. He claimed Jenkins's command had captured and paroled near 300 prisoners of war, killed, wounded, and dispersed about 1,000 of the enemy, reclaimed about 40,000 square miles to Confederate control, and destroyed at least 5,000 stand of small arms, one piece of cannon, and immense stores. Federal General Jacob D. Cox would later write that 'little real mischief was done' but conceded that the raid contributed to what he called Lightburn's 'embarrassing' retreat. Within a month, Cox would be back in the Kanawha Valley as a major general, retaking Charleston by October 30. The fates of the principals followed familiar Civil War arcs. Lightburn was reassigned to Sherman's XV Corps, promoted to brigadier general, lightly wounded in the face on August 24, 1864, and resigned in June 1865. Cox became governor of Ohio after the war, served as Grant's Secretary of the Interior, and returned to Congress. Jenkins did not survive. He led a brigade at Gettysburg, was wounded on July 2, 1863, recovered, returned to West Virginia operations, and was mortally wounded at the Battle of Cloyd's Mountain on May 9, 1864. He died twelve days later on May 21, 1864, in Dublin, Virginia. The trans-Allegheny raid was the high point of his military career.