The raid was originally proposed by John Hanson McNeill, the partisan commander of McNeill's Rangers, who wanted to destroy at least one critical B&O bridge. Confederate command expanded the plan into a two-pronged attack. Brigadier General William E. "Grumble" Jones - whose nickname referred to his irascible temper and his profanity-laced tirades - would attack the B&O between Grafton and Oakland, Maryland with about 3,500 cavalry. Brigadier General John D. Imboden would attack Union garrisons at Beverly, Philippi, and Buckhannon with infantry and mounted infantry totaling about 3,365 men. The political motive was as important as the military one: West Virginia voters had approved a new state constitution in March 1863, and President Lincoln issued the statehood proclamation on April 20 - the same day the raid began. The Confederates were trying to disrupt the soon-to-be state before it could function.

On April 26, Jones reached the Cheat River and sent Captain Octavius T. Weems of the 11th Virginia Cavalry with fewer than 100 dismounted men over Palmer's Knob to descend on Rowlesburg from above. The Confederate troopers came down the mountain, an eyewitness later wrote, "bounding and bellowing down the mountain, yelling like fiends just up from the pit." The Union garrison and the Rowlesburg townspeople were ready. Concealed behind the railroad embankment with Enfield rifles, they let the Confederates close to easy rifle range before opening fire. Cannons on Cannon Hill, 600 feet above the valley with clear sight lines, joined the defense - the artillery had been hauled up the slope by oxen. Within half an hour, Weems' force was in full retreat. Jones tried again with his main column moving up the River Road from Macomber, but Lieutenant McDonald's Union riflemen, joined by Lieutenant Hathaway's Company K reinforced by about 20 local citizens, held a log barricade through six hours of fighting. By dusk, Jones accepted defeat. The bridge stood. The cavalry that had ridden into West Virginia to destroy Lincoln's Lifeline rode away unable to.

Imboden's column had its own difficulties. He marched westward from Shenandoah Mountain on April 20 through heavy rain and then snow, defeating Union defenders at Beverly under Colonel George Latham and capturing supplies the retreating Federals had to abandon. By April 28, he had taken Buckhannon after the Union commander, Brigadier General Benjamin S. Roberts, ordered a withdrawal to Clarksburg. In Washington, the Union general-in-chief Henry Wager Halleck was infuriated. He wired General Robert C. Schenck: "The enemy's raid is variously estimated at from 1,500 to 4,000. You have 45,000 under your command. If you cannot concentrate enough to meet the enemy, it does not argue well for your military dispositions." To Roberts at Buckhannon, Halleck wrote: "I do not understand how the roads there are impassable to you, when, by your own account, they are passable enough to the enemy." On April 29, Imboden met Jones on the march, and the two columns combined briefly.

After parading through Weston on May 5 - where Imboden took the chance to send his parents to safety behind Confederate lines - the generals decided against attacking the larger town of Clarksburg, where Union reinforcements had concentrated. Instead, they split again. Imboden moved south with the captured supplies and wounded. Jones rode northwest to West Union and Cairo, where he burned five more railroad bridges and disabled a railroad tunnel. The most dramatic destruction came at Burning Springs - then known as Oiltown - where Jones's troops demolished the oil field equipment and burned 150,000 barrels of crude oil. The smoke could be seen from miles away. Burning Springs had been one of the earliest American oil fields, with oil drilling underway in 1859 - the same year as Edwin Drake's first commercial well in Pennsylvania. The Confederate raid effectively ended its career as a producer for the rest of the war.

In his final tally, Jones counted 16 bridges destroyed, 30 Union killed, 700 prisoners taken, 400 new Confederate recruits, 1,200 horses, 1,000 head of cattle, an artillery piece, and the destroyed Burning Springs oil works. Tactically, the raid was a substantial Confederate success. Strategically, it failed at every level. The Cheat River bridge - Lee's prize - survived. The Wheeling suspension bridge across the Monongahela survived. Senator Waitman Willey, a key Unionist figure, escaped across the Ohio in a fast buggy. Governor Francis Pierpont's library at Fairmont was burned, but the Restored Government of Virginia continued to function. Most damaging to the Confederate cause: the raid had no effect on the statehood movement. West Virginia was admitted to the Union as the 35th state on June 20, 1863, less than three weeks after the raid ended. The greater part of Imboden's troops and many of Jones's came from western Virginia. Their own homes were now in a state they had been raiding against. Neither the Confederate government nor the secessionist Virginia government in Richmond ever recognized West Virginia's statehood. They did not need to. The Union held the new state for the rest of the war.