Rain continued to fall on the third day of the Union march. Again, Custer’s division took the lead, and at Mount Crawford they ran into a familiar foe, Tom Rosser, who had scraped together a couple hundred cavalrymen and was busy setting fire to the covered wooden bridge across the North River. Custer called for Colonel Henry Capehart, commander of the 3rd Brigade, and ordered him to secure the bridge at all costs. Capehart had just joined Custer’s division after a transfer from the 2nd Division, and he was understandably eager to make a good impression. He quickly had two regiments swim across the river above the bridge, while he personally led the rest of the brigade in a high-throated charge across the burning timbers. Rosser’s men fired a last volley at the oncoming Federals and melted back into the woods, but not quickly enough to prevent the capture of 37 Southerners.

Subscribe Today

• Did you enjoy our article?
• Read more in America's Civil War magazine
• Subscribe online and save nearly 40%!!!
 

That night the Federals bedded down in an icy shower at Cline’s Mill, seven miles north of Staunton. Sheridan ordered Colonel Peter Stagg’s Michigan brigade to skirt Staunton in the dark and burn the railroad bridge to the east at Christian Creek to prevent the Rebels from evacuating the town. Stagg’s troopers successfully burned the bridge after piling fence rails on top of the span, but they were too late to stop the evacuation. Early and his staff had ridden out of Staunton at 3:45 that afternoon, headed for a fateful rendezvous with Brig. Gen. Gabriel C. Wharton’s ragtag infantry division at Waynesboro, a small village midway between Staunton and Charlottesville on the banks of the South River near Rockfish Gap in the Blue Ridge Mountains.

The next morning Sheridan entered Staunton. The streets were deserted, the warehouses empty, but somehow Early had left word for his old adversary that he intended to fight at Waynesboro — or at least that is what Sheridan reported later. It seems doubtful that Early, leaving in haste with an army eight times the size of his snapping at his heels, would have been so bold as to invite further pursuit. Probably, Early expected Sheridan to continue south to Lynchburg, where ‘Jube’ had already dispatched his largest infantry force. Sheridan later explained that he was reluctant to leave Early’s troops — all 1,200 of them — in his rear, although what possible harm they could have done in their present worn-down state was anyone’s guess. Still, if Early wanted to fight at Waynesboro, Sheridan would be more than happy to accommodate him. Besides, each step Sheridan took to the east carried him that much closer to Grant — and that much farther away from Sherman. All in all, it seemed like a good trade-off.

Sheridan summoned Custer and told him, Custer reported, to ‘ascertain something definite in regard to the position, movements, and strength of the enemy, and, if possible, destroy the railroad bridge over the South River at that point.’ Since Sheridan already knew how many men Early had and where he had gone, the order did not make much sense, but it was all Custer needed to mount up and head east.

In the meantime, Early had reached Waynesboro and set about preparing a makeshift defensive line on a low ridge west of town. General Wharton, a veteran of every major valley fight since the Battle of New Market, was given the unenviable task of holding down a three-quarter-mile-long line of rifle pits with a skeleton force of 1,000 infantry, 100 cavalry and six artillery pieces. The thin-stretched line was a mere 200 yards from the rain-swollen South River, and the sleet-soaked Confederates were uncomfortably aware of the raging watercourse to their rear. To make matters worse, the line did not stretch far enough south to touch the westward bend of the river — a gap of about an eighth of a mile that left the Rebel flank hanging in the air. Captain Jedediah Hotchkiss, Early’s New York–born topographical engineer, charged later that Early had ‘committed an unpardonable error’ in posting his troops in such an exposed position. Early explained, rather lamely, that he had placed the men there in order ‘to secure the removal of five pieces of artillery for which there were no horses, and some stores still in Waynesboro, as well as to present a bold front to the enemy, and ascertain the object of his movement, which I could not do very well if I took refuge at once in the mountain. I did not intend making my final stand on this ground, yet I was satisfied that if my men would fight, which I had no reason to doubt, I could hold the enemy in check until night, and then cross the river and take position in Rockfish Gap.’

Help HistoryNet by bookmarking to