Following an unsuccessful attack on Washington D.C. on July 11, 1864, Confederate General Jubal A. Early withdrew to the Shenandoah Valley, where he had left Gen. John C. Breckinridge’s division to hold the Shenandoah River fords. Union General George Crook pursued Early but was repulsed when he sought to cross the river at Castleman’s Ferry on Sunday, July 17.
A Confederate deserter well acquainted with the area guided Union forces under Colonel Joseph Thoburn through woodlands north to the site of the Retreat, the home of Judge Richard Parker, where they were able to cross the river late in the afternoon of July 18 virtually undetected and form a battle line in the woods behind a stone fence on Cool Spring Farm (present-day Holy Cross Monastery).
When Breckinridge learned of the Union advance he sent Generals John B. Gordon’s and Gabriel C. Wharton’s divisions to challenge the attack. Confederate General Robert E. Rodes joined the offensive on the Unions right flank. Faced with superior forces Union troops retreated back across the river, losing 422 killed, wounded, and missing. Confederate casualties totaled about 295. Despite withstanding the Union assault, General Early continued to move his forces westward toward Winchester.
