Yankee Cavalry Captures an Entire Rebel Regiment

September 13, 1864 (Tuesday)

The day previous, William Averell’s cavalry scouts learned much of the enemy’s position near Bunker Hill, just north of Winchester, Virginia. In writing to Philip Sheridan, Averell described the findings:

Today, McIntosh will be everywhere!
Today, McIntosh will be everywhere!

A negro woman came in on the direct road from Winchester, who lives near the Gerrardstown road, last evening with a pass signed by command of Major-General Lomax, dated yesterday. She had been arrested on Saturday, charged with giving information to us. She says she left General Lomax’s headquarters yesterday; he was one mile and a half north of Winchester on this pike. Early’s headquarters were at Stephenson’s Depot; Breckinridge’s, six miles this side of Winchester, division encamped on both sides of the road in line, but with no breast-works; Wharton, half a mile north of Breckinridge, at Reeder’s, encamped on both sides road; Rodes’ division three miles south of Bunker Hill, t. e., nine miles from Winchester.

If true, and there was really no reason to doubt this woman, Jubal Early had arrayed his army along the Valley Pike, mostly facing Opequan Creek.

Very approximate today, folks!
Very approximate today, folks!

Along the line much closer to Winchester was the Confederate division under Joseph Kershaw. The entire division had been attempting to leave the Valley to possibly rejoin General Lee’s main body in Petersburg. The week previous, it had been caught up in a skirmish, but it was looking like this day would be a good one to make the escape. It was not.

Sheridan was leery of whatever was going on in Winchester. The bulk of Early’s army was well to the north, but lingering to the south was an entire division. To suss this out, he ordered James Wilson, commanding a cavalry division, to dispatch a brigade to see what they could see. Wilson selected John McIntosh, ordering him to “make a strong reconnaissance toward Winchester for the purpose of determining enemy’s position.”

As McIntosh’s brigade rode forward, taking the Berryville Pike toward Winchester, they met Confederate pickets on a ridge just east of the Opequon. McIntosh devised a plan with the hopes of enveloping and capturing them. “The enemy,” he wrote, “frustrated the movement by hastily evacuating the ridge.”

Where McIntosh crossed the Opequon - post-war shot.
Where McIntosh crossed the Opequon – post-war shot.

With nothing before him but the creek, he crossed it, moving swiftly west, and came upon the Rebel cavalry posted on a hill and in some woods. The Confederates were aligned and dismounted, “and gave my advance regiment, the Second Ohio, a hot fire.” In response, McIntosh slid them left, trying to outflank the Southerners.

“As soon as the enemy discovered my movement he hastily withdrew. I then pushed on rapidly over the main road, which ran through a ravine with high hills on each side and very wooded. In advancing rapidly, I overtook some of their dismounted men, who had secreted themselves in a thick skirt of woods.” A New Jersey regiment went in and came out with upwards of thirty prisoners. All the while, McIntosh pushed forward.

Before long, word from his own advance scouts had it that there was infantry before him. But he was hardly intimidated.

“I immediately rode on a hill to the line of skirmishers, saw their force, and sent word to Colonel Suydam of the Third New Jersey Cavalry, to charge one squadron up the road as hard as they could go, and at the same time charged my skirmishers as foragers.”

James Conner!
James Conner!

From the report of Confederate General James Conner, commanding the brigade, as taken from the word of those who escaped:

The Yankee cavalry advanced (mounted) and deployed in front of the main picket; another portion deployed considerably to the left of the main picket; another portion advanced in column at a gallop up the pike, and receiving a volley from the picket dashed past it. Colonel Henagan then fell back into the woods in rear of his picket station, reformed his men, and moved through the woods to the edge of the timber on this side.

“Gaining that point they perceived the Yankee cavalry in front of them; these they fired upon and drove back. Advancing from the woods with the view of coming back to the brigade, they were again met by a considerable body of Yankee cavalry and Colonel Henagan fell back into the wood, some desultory firing going on between his men and the Yankees.

“While this was taking place the Yankee cavalry that had deployed in his front at the commencement (now in his rear) dismounted and advanced into the woods, while the other cavalry rode around the edge of the timber shouting to our men to come out. When the dismounted cavalry were within 50 or 100 yards of our men in the woods the latter surrendered.

“The prisoners were immediately hurried off, the officers of the Yankee cavalry urging their men to be expeditious. The two companies on duty at the picketpost to the right, after skirmishing with the advancing enemy, fell back and escaped,- with the exception of three or four men, who were acting as vedettes at the mill.”

When McIntosh’s Federals surrounded the Rebel regiment, they captured their colonel as well as the battleflag.

Though about to march out of the Valley, Kershaw ordered forward a brigade under James Conner to rescue the South Carolinians. But it was too late. “I dispatched the Third [South Carolina] Regiment to his relief,” wrote General Connors, “with orders to the brigade to follow, and galloped forward myself toward the picket, but as I rose the hill from my camp I saw the Yankee cavalry in rear of our picket. The courier who brought me the intelligence never got back to Colonel Henagan.”

There was now no chance for Kershaw to make his egress. Richard Anderson, commanding the corps in place of the wounded James Longstreet, was with this division and had something to say about the Eighth South Carolina.

“The conduct of Col. Henagan and his regiment on this occasion is inexcusable,” he wrote. “The post was one which might have been defended for some time against any odds.”

Though delayed, it would only for a day. Kershaw would leave the following day, sapping Early’s strength to 15,000. Sheridan, with 40,000, would certainly take notice.1



  1. Sources: Official Records, Series 1, Vol. 43, Part 1, p517, 529-530, 592-593; Part 2, p79, 80; The Last Battle of Winchester by Scott C. Patchan. []
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Yankee Cavalry Captures an Entire Rebel Regiment by CW DG is licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 4.0 International

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