On May 2, 1864, Sigel marched south from Winchester with 9,000 men. Union general-in-chief Ulysses S. Grant, who understood the Valley’s importance in sustaining Lee’s army through men and supplies, directed Sigel to clear the area of Confederates. Lee gave the responsibility of confronting Sigel to a former United States senator from Kentucky and vice president under James Buchanan who, as a proslavery, states’-rights moderate, had come in second behind Abraham Lincoln in the U.S. presidential election of 1860. Breckinridge lacked formal military training but had acquitted himself well in the Western Theater at Shiloh in 1862 and Chickamauga in 1863. Now, however, he was outnumbered and forced to muster hastily whatever forces he could find. His skeletal army that spring numbered only about 5,300 troops, which included two brigades of infantry, 1,500 cavalrymen under General John D. Imboden, and 257 VMI cadets commanded by Colonel Scott Shipp. “I trust you will drive the enemy back,” Lee told him.
On May 11, Imboden captured 464 Union cavalrymen near Port Royal. The next day Breckinridge’s main force reached Staunton but stayed only a day before marching north to meet Sigel. The slow-moving Union forces, fighting off Imboden’s horsemen, arrived in the area around Woodstock and Mount Jackson on May 14. Several miles to the south, meanwhile, was New Market, population 1,422, a farming village that sat at the crossroads of the Valley Turnpike and the only road over Massanutten Mountain to the east. Sigel coveted control of New Market Gap because it would allow his forces quickly to cross the Blue Ridge and swoop down on Lee’s left flank. For the moment, though, he was bogged down by heavy spring rains that had washed out nearly all the roads except the macadamized Pike.
On the morning of May 14, 1864, Imboden’s cavalry engaged a detachment of the 1st New York Cavalry just northwest of New Market, where the Union horsemen were attempting to secure a bridge over the North Fork of the Shenandoah River. Sigel reinforced the New Yorkers with a brigade of infantry under Colonel Augustus Moor and an overwhelmed Imboden was forced to retreat to New Market that evening. Early the next morning, Breckinridge arrived from Lacey’s Springs and sent both cavalry and artillery against Moor in an attempt to lure the Union forces into attacking him. After a heated artillery duel, Breckinridge advanced on the Union line at ten o’clock, pushing Moor’s men back while Imboden’s cavalry attacked the Union left flank, pressing east to get around Sigel’s left and cut off his only avenue of withdrawal.
Sigel, a German-born general with a much greater gift for politics than for warfare, arrived on the battlefield at eleven and ordered Moor’s Connecticuters and Ohioans back. As they abandoned New Market, Breckinridge’s men marched through town and took up positions to the north. By two o’clock, through a driving rainstorm, blinding smoke, and deepening mud, they had pushed the Union forces all the way back to Bushong Hill. There, Sigel deployed eighteen of his guns and aimed them at Breckinridge’s still-advancing line. They wreaked a predictable havoc, especially on five Virginia regiments that were thrown back from the Bushong Farm.
By 2:40 p.m. the Confederate advance had faltered, and at 3 p.m. Sigel organized a hasty and uncoordinated counterattack of infantry under Moor and Colonel Joseph Thoburn and cavalry under General Julius Stahel. “I dinks we fight him a little,” Sigel told one of his gunners, and indeed he was now taking the battle to Breckinridge. The problem for Sigel was that much of his army was still marching along the Valley Turnpike, en route to New Market. When his attack was stymied by Confederate artillery and sharpshooter fire, he had no reinforcements on which to call. And his artillery batteries, including one commanded by Captain Albert von Kleiser, suddenly became vulnerable. Breckinridge saw his chance.
Shortly after three o’clock, the Confederate general ordered another attack on Bushong Hill, this time calling in the boys from VMI. “They are only children,” he had told an aide earlier in the day, but in fact their average age was eighteen, and reminiscent of the “foot cavalry” made famous two years earlier by Thomas J. “Stonewall” Jackson they had marched eighty miles from Lexington to New Market in just a few days. When a hundred-yard-or-more gap in the Confederate lines opened up where the Virginians had retreated under heavy artillery fire, Breckinridge used the cadets to plug the hole and sent them after the Union battery. The cadets charged across a field so muddy that some of their shoes were sucked off their feet—hence the legendary “Field of Lost Shoes”—and eventually they were able to take Kleiser’s battery and even a few members of the 34th Massachusetts. Sigel’s men began to panic, with Sigel himself riding up and down the line, “all jabbering in German,” as one of his officers recalled, so that “the purely American portion of his staff were totally useless to him.”
The main body of Sigel’s army fell back to Rude’s Hill, while his regiments east of the Valley Turnpike, with the help of Captain Henry DuPont’s battery, covered the retreat. In the face of DuPont’s fire, Breckinridge halted the Confederate advance at about four o’clock. He was soon met by Imboden, who reported that he had failed to maneuver behind the Union troops and destroy that bridge over the Shenandoah River. The last of Sigel’s troops crossed over at seven, burning the bridge behind them. Marching all night and through the next day to distance himself from the Confederates, Sigel arrived at Strasburg on the evening of May 16. He had suffered 831 casualties, including 256 missing (most of them captured) and 96 men killed, while Breckinridge’s casualties numbered 577, including 43 killed, 10 of whom were VMI cadets.
The battle and the subsequent retreat of Sigel’s army successfully secured Lee’s left flank, and Breckinridge marched his small force east to reinforce the Army of Northern Virginia. The cadets went along as far as Richmond before returning to VMI on June 10. Also in June, Confederate general Jubal A. Early took advantage of the cleared-out Valley to march his newly created Army of the Valley all the way to the outskirts of Washington, D.C. Sigel, beloved by a large and important constituency of German-Americans, had up to then managed the political end of his military appointment brilliantly; now the military end of his military appointment caught up with him, and Lincoln relieved him of his command. The Valley, meanwhile, played host to the Shenandoah Valley Campaign of 1864 in which Sigel’s successor, Union general David Hunter, employed hard-war tactics, which included the burning of VMI on June 12.