On May 21, 1862, Confederate Gen. Thomas J. “Stonewall” Jackson’s Valley Army moved north along this road to threaten Front Royal and outflank Union Gen. Nathaniel Banks’s position at Strasburg. Reinforced by Gen. Richard S. Ewell’s division, Jackson’s command numbered nearly 17,000 men and 50 guns. Philip Kauffman later recalled the Confederates crossing the Shenandoah River on White House Bridge and seeing Jackson ride past the White House on Old Sorrel through the marching columns of his “foot cavalry.” Jackson’s army reached Front Royal on May 23 and, aided by spy Belle Boyd, overwhelmed Banks’s 1,000-man detachment there before continuing toward Winchester to strike the main Union army, which was retreating from Strasburg. Jackson drove Banks from the Valley and alarmed the Lincoln administration. In response, a two-pronged Federal advance was ordered to converge at Strasburg to cut off Jackson’s withdrawal to the south, with Gen. John C. Fremont advancing on the Valley Pike and Gen. James Shields in the Page Valley. To prevent Shields and Fremont from combining, Jackson ordered cavalry commander Turner Ashby to destroy White House Bridge and Columbia Bridge. Ashby sent Capt. Samuel Coyner’s Page County Company, which rode through a severe thunderstorm and burned White House Bridge at 4 a.m. on June 2, only an hour before Shields’s advance guard reached the swollen river. Delayed three days by the rising river, Shields had to abandon his plan to join Fremont at New Market, and Jackson then defeated Fremont’s and Shields’s commands separately at Cross Keys and Port Republic on June 8-9. White House Bridge was named for the small building just north of the present-day bridge, the first home of pioneer Martin Kauffman, which for a time also served as a meeting house for a Mennonite congregation he ministered.