On January 1, 1864, eighty members of Cole's Maryland Cavalry, led by Captain A. M. Hunter, entered the region colloquially known as "Mosby's Confederacy" around Upperville and Rectortown, Virginia.

Within a week, Cole's camp atop Loudoun Heights had been discovered, thanks to the work of Benjamin Franklin Stringfellow, a staff officer under J.E.B.

The partisan company set out for Loudoun Heights through deep snow and bitter cold, reaching Woodgrove around 8 p.m. and stopping for 2 hours at the home of Ranger Henry Heaton.

Spotting Federal pickets posted along the Hillsboro-Harpers Ferry Road, the Confederates turned and headed east toward the wooded western slope of Short Hill Mountain, which they followed until they came to the bank of the Potomac River.

In the confusion of the 45 minute fight that followed, several Rangers retreated and, soon afterward, with the sound of Federal infantry approaching from Harpers Ferry, Mosby ordered a general withdrawal.

The Rangers escaped with 6 prisoners (pickets from Co. B of Cole's Cavalry, all taken from their post along the Hillsboro road at the crossing of Piney Run) and nearly 60 horses, but were forced to leave their dead and seriously wounded behind.

A few miles beyond the Union camp, Mosby halted and sent two Rangers back under a flag of truce to exchange the prisoners for their dead and wounded, which included Billy Smith and First Lieutenant Thomas Turner.