Following the Union defeat at the Second Battle of Bull Run [Second Manassas], Confederate General Robert E Lee decided instead of pursuing his opponent into their fortifications near Washington he would turn and move into Loudoun County, reorganize and plan his invasion into Maryland. At the time Loudoun was occupied by Union troops operating out of Harpers Ferry. Lee ordered General J E B Stuart’s cavalry into Loudoun in advance of the army’s movement as a screen.
The 2nd Virginia Cavalry under the command of Confederate Colonel Thomas T Munford was sent to secure the river crossings and town of Leesburg, Virginia. On September 2nd 1862 as Munford approached the town, he split his command sending a squadron commanded by Captain Jesse Irvine Jr directly into town, while the rest of the regiment moved toward Edward’s Ferry. Irvine moved into town and ran into the Union Loudoun Rangers at the courthouse. The Rangers fell back to the north end of town and the position being held by Cole’s Maryland Cavalry. Cole’s men were fighting dismounted and began engaging Irvine. About that time Munford’s command attacked the Union men from their rear, having flanked them from the river and approaching via Smart’s Mill Lane. Cole had his command attempt to mount but may of the men were killed or wounded before they could get to their horses.
Those Union men who got to their horses briefly engaged Munford. They retreated towards the Catoctin Mountains, reaching the road to Waterford and a gap in the mountain. The Confederates chased Cole’s men for two miles. The Union cavalry had 7 killed, 33 wounded and 15 captured, while the Confederates lost 2 killed and 5 wounded.