Although Confederate Maj. Gen. Thomas J. “Stonewall" Jackson was pleased with his May 23, 1862, victory at Front Royal, he was faced with a difficult decision the next day. “In the event of Banks leaving Strasburg he might escape toward the Potomac," he wrote later, “or if we moved directly to Winchester, he might move via Front Royal toward Washington City." To determine US Maj. Gen. Nathaniel Banks’s intentions, Jackson sent troops toward both Winchester and Strasburg.
Armies Converge on Middletown
The morning of May 24, 1862, Jackson ordered Brig. Gen. George Steuart’s Virginia cavalry to Newtown (now Stephens City), about ten miles north of Banks’s base at Strasburg, to see what he could find. What Steuart found was an endless line of Federal supply wagons heading north on the Valley Pike to Winchester. Confederate troops smashed into this line of wagons, the teamsters fled, but strangely enough, the Confederates did not burn the wagons, a move that would have blocked the Pike.
Steuart then led his men south toward Middletown. As Steuart’s cavalrymen rode south from Newtown, they ran into Federal infantry - Banks’s main force - which scattered the Confederates, and the Federal retreat north continued. Among this Federal column was most of Banks’s infantry, some of his artillery, and Banks himself.
Hearing about what Steuart’s men had found, Jackson decided to further split his command; he sent orders to Maj. Gen. Richard Ewell to advance tentatively on the Cedarville Road towards Winchester, while ordering Brig. Gen. Richard Taylor to take his Louisiana brigade, with some artillery and cavalry under Col. Turner Ashby, west on the Chapel Road to Middletown. Around 3:30 p.m., as Taylor’s column neared the Valley Pike north of the town, more of the Federal wagon train moving north came into view.
Taylor ordered his artillery to unlimber and fire at the wagons. Again, the damage to the Federal wagon train was terrific, and most of the teamsters fled. When Jackson arrived about a half-hour later, while pleased with the destruction, he was more interested in locating the Federal infantry. To determine this, he ordered Taylor south, through Middletown, to see if Banks’s main force was marching north from Strasburg.
The Running Fight
As Taylor’s men advanced, many of them looted the abandoned wagons, but upon approaching the southern end of Middletown, the Louisianans received enemy fire. “As we jumped over the stonewall into the pike, a vicious volley of bullets whistled through our disordered ranks, splintering the rails of the neighboring fence and wounded several of my comrades," Pvt. Henry Handerson of the 9th Louisiana remembered, “and looking down the road towards Strasburg, I saw a company of Zouaves firing vigorously upon our advance."
Those Zouaves were members of Col. Charles H.T. Collis’s Zouaves d’Afrique, a company of about one hundred soldiers who formed Gen. Banks’s headquarters guard. Although Banks had already ridden north, he had ordered Collis to stay behind with the rearguard, see that the rest of the wagon train got out of Strasburg, and that anything of military value left behind be destroyed.
Collis led his men to a stone wall perpendicular to and along the right side of the Valley Pike at the southern end of Middletown. As the Louisianans approached, Collis’s men opened fire. Oddly enough, many of these Confederates were also attired in Zouave uniforms; they were members of Maj. Roberdeau Wheat’s special Louisiana Battalion, better known as the Louisiana “Tigers."
Zouaves versus Tigers
Collis’s men fired three volleys, then fell back to a ridge about a half-mile south, across the pike from the Belle Grove Plantation, taking position to the right of Capt. R.B. Hampton’s Battery F, Pennsylvania Light Artillery (Hampton had four 10-pound Parrott rifled guns). Soon joining Collis and Hampton were five companies of the 1st Vermont Cavalry, and a bit later, six companies of the 5th New York Cavalry.
Taylor’s Louisianans tested the Federals from a distance, but did not seriously challenge them, allowing the Union force to pull back south across Cedar Creek, and up Hupp’s Hill, one mile shy of Strasburg, where they expected to be attacked. Collis and the rest of the rearguard eventually moved west, then north, to reunite with the rest of Banks’s command. Unable to find Banks, they continued all the way to the Potomac River, reaching Hancock, Maryland, around 2 p.m. on May 26th. They had marched over 140 miles in under two days.
By 5:45 p.m. of the 24th, Jackson realized that his men only faced a rearguard, and he ordered Taylor to turn around and head north. He also sent word to Ewell, still on the Cedarville Road, to do the same. It now remained to be seen whether Jackson could catch Banks’s main column before the Federals reached the hills south of Winchester.
Federals Escape Disaster
The Confederates could not catch up to Banks’s men. Although they passed dozens of captured or abandoned wagons - “the streets were lighted up by the burning of a commissary train, especially the flames from the burning bacon and from wagonloads of rice," one Confederate recalled - they couldn’t catch Banks’s infantry. Forming the Federal rearguard were the 2nd Massachusetts, 27th Indiana, and 28th New York Infantry Regiments. These units held the Confederates off as the retreat to Winchester continued.
When the men of both armies neared Winchester, the Federals occupied positions on the hills south of town, and the Confederates stopped just north of Kernstown, some units not reaching their destinations until the early morning hours of May 25th. But for all present, whether wearing blue or gray, they collapsed from exhaustion. The fight was not over, though; it would be continued later that day.
Source: U.S. Department of the Interior, National Park Service