Battle of Mile Hill The Battle of Mile Hill was a cavalry skirmish during the American Civil War , that took place just north of Leesburg , Virginia , on September 2 , 1862 . It preceded the occupation of the town by the Army of Northern Virginia just prior to its crossing of the Potomac River starting the Maryland Campaign . Confederate cavalry under Col . Thomas T . Munford surprised and routed the Federal force of Cole ' s Maryland Cavalry and the independent Loudoun Rangers . The engagement successfully cleared the area of Federal forces , allowing Robert E . Lee and the Army of Northern Virginia to occupy the town two days later on September 4 , before crossing the Potomac north of town on September 6 . Background . After the failure of Army of Northern Virginia to deliver a decisive blow to the Army of Virginia at the Battle of Ox Hill following the Second Battle of Bull Run , Robert E . Lee decided it unwise to pursue the Federals any further towards their fortifications near Washington D . C . . Instead , he planned to move into Loudoun County to obtain forage and provisions and to reorganize the army before his planned invasion of Maryland . At the time , Loudoun County was occupied by Federal troops operating from the Union garrison at Harpers Ferry . As such , J . E . B . Stuart ' s cavalry was sent in advance to screen the army ' s movements and to clear Loudoun of enemy resistance . To this end , on September 1 , the 2nd Virginia Cavalry , under the command of Col . Thomas T . Munford , was assigned to secure the town of Leesburg and the river crossings in its vicinity . Battle . The following day , as Munford approached the eastern end of Leesburg , he split his command , sending a squadron under the command of Captain Jesse Irvine , Jr . directly through town , while he , with the rest of his regiment turned north off the Leesburg Pike ( present day Route 7 ) towards the Edward ' s Ferry river crossing . Irvine and his command rushed into town to find Samuel C . Means and his Unionist Loudoun Rangers guarding the courthouse . The Rangers , having been severely manhandled by E . V . White and his partisan Rebels a few days prior at Waterford , put up little resistance before retreating north up King Street ( 15 ) , though not before suffering four wounded . The Rangers fell back on Cole ' s Maryland Cavalry , who were positioned to the north of town at the Big Spring ( near present day Tutt Lane ) , with Irvine ' s command in hot pursuit . Cole ' s dismounted command began to engage Irvine , but moments later Munford ' s command attacked from their rear flank , having been able to circumvent the Union position by riding around its left flank along the river and approaching its rear via Smart ' s Mill Lane , which Cole had foolishly left unguarded . Cole attempted to mount his command to engage Munford , but many of his troops were killed or wounded before they could reach their horses . Those that did , briefly engaged Munford before retreating towards the Catoctin Mountain and the road to Waterford , which cut through a gap in the ridge . Munford gave chase for two miles , driving the Federals through the gap into Loudoun Valley before retiring , having successfully cleared Leesburg and the river crossings in its vicinity . Results . Of Munford ' s 163 troops on the field , he suffered 2 killed and 5 wounded , while of the Loudoun Rangers 30 or so men , 1 was killed , 6 were wounded and 4 captured . Cole ' s Cavalry , estimated at 150 strong , reported 6 killed , 27 wounded , and 11 captured , though a significant amount of those casualties were officers . Battlefield . The main portion of the battle started approximately where the present day U . S . Rt . 15 Bypass converges with Business Rt . 15 near the Harrison Farm ( this being Cole ' s initial position ) . The battle then moved southwest across present day Morven Park and Ida Lee Park to Old Waterford Road . None of the battlefield is protected as such , but Morvin Park remains undeveloped , as does much of Ida Lee Park , so if one follows the Civil War Trails signs to the historical marker off of Tutts Lane , a good feel for the setting of the battle can be had . Cole ' s initial position has been mostly obliterated by construction and widening of the Rt 15 highway system , as well as the partial condemnation of the Harrison Farm by the public school system to build Smart ' s Mill Middle School and Frances Hazel Reid Elementary School . Likewise , the approach Munford took up Smart ' s Mill Lane has become a housing development , though a piece of the old road survives within the modern subdivision .