Loudoun County was involved in the Civil War long before the first shots were fired by John Brown’s raiders in Harpers Ferry in 1859. Throughout the 1840s and ‘50s, the county was a pathway on the so-called “Underground Railroad” that took escaped slaves from Southern states to freedom in the Northern states and Canada. The heavily timbered Blue Ridge Mountains on the county’s western border offered abundant hiding places for escapees, while free blacks in communities near the Carolina Road, Quakers, and other Abolitionists in the county stood ready to help out with food, medical attention, and directions to the nearest fords across the Potomac River.
Loudoun was a county of divided loyalties. The English Cavaliers who first settled the eastern and southern portions brought with them their practice of farming large tracts of land with slave labor, while the Quakers, Germans, and Scots-Irish who moved into the northern end of the county from Pennsylvania and points north worked self-sustaining family farms. The result was a division in the county between loyalty to the Union and a desire to join the new country being formed by Deep South cotton states. When the Virginia secession vote was finally taken by the people on May 23, 1861, almost one in three Loudoun residents cast their votes in favor of remaining in the Union. Still, Loudoun contributed companies of men to seven different Confederate regiments and individual members to several more.
Once Virginia decided to leave the United States, Loudoun found itself on the border between two hostile nations. Unlike neighboring Fairfax and Arlington counties, Loudoun was not immediately occupied by Union troops, but it was threatened by Northern units stationed near Poolesville and Harpers Ferry. In June 1861 the bridges across the Potomac River at Harpers Ferry, Berlin (now Brunswick) and Point of Rocks were burned. The bridges may have been down, but the county was still vulnerable at nearly 20 useable fords.