After defeat at Bristoe Station and an aborted advance on Centreville, Stuart’s cavalry shielded the withdrawal of Lee’s army from the vicinity of Manassas Junction. Union cavalry under Kilpatrick pursued Stuart’s cavalry along the Warrenton Turnpike but were lured into an ambush near Chestnut Hill and routed. The Federal troopers were scattered and chased five miles in an affair that came to be known as the "Buckland Races."

On October 19, 1863, 12,000 Confederate and Union cavalry clashed at the Battle of Buckland Mills in the last large-scale Confederate victory in Virginia. Gen. J.E.B. Stuart, screening the Confederate infantry's march to Culpeper County, blocked Union Gen. H. Judson Kilpatrick's advance at Buckland, then withdrew west. Union Gen. Henry E. Davies's brigade pursued Stuart while Gen. George A. Custer's brigade occupied Buckland. Gen. Fitzhugh Lee suddenly attacked Custer from the south, isolating the two brigades, and Stuart charged Davies. The Federals fled east. The Confederates called the engagement the "Buckland Race."

On the morning of October 19, 1863, two cavalry commands occupied this ground in succession. Confederate Gen. J.E.B. Stuart and his men held it from about 10 A.M. until noon before withdrawing west along the Warrenton Turnpike as Union Gen. George A. Custer's cavalry brigade approached from your left. Custer occupied this position while Gen. Henry E. Davies's brigade passed, lured west by Stuart.
Early in the afternoon, as Custer's men rested in the then-open fields before you, Confederate Gen. Fitzhugh Lee's division struck from the woods to your right front, pushing Custer back here and separating his brigade from Davies's at New Baltimore. Lee drove Custer east from here across the Broad Run bridge toward Gainesville, and the Confederates held this ground again by evening. Lee pursued Custer until long after dark, and Stuart drove Davies beyond Broad Run upstream from here.
The Confederates lost about 50 men, the Federals about 260, mostly prisoners. Stuart termed the rout, his last victory over cavalry, "the most complete that any cavalry ? suffered during this war." Custer called the day "the most disastrous this division ever passed through."

Founded in 1797, Buckland became a thriving community with two mills, a large distillery, and several taverns. The Warrenton-Alexandria Turnpike and a pest-resistant strain of wheat developed here added to the town's prosperity. During the war, the turnpike bridge became a military objective. On August 27, 1862, during the Second Manassas campaign, Union Gen. Robert Milroy's brigade, marching toward Gainesville, found the Broad Run bridge on fire and Confederate cavalry with one piece of artillery on the opposite side. Milroy's cavalry detachment drove them off. The men quickly repaired the bridge so that parts of Union Gen. John Pope's army could march across it to Manassas. The war forced many of the businesses in town to close.