John Divine, a local historian, did extensive research about Civil War battles in Loudoun County, including the battle of Miskel's Farm. On March 31, 1863, Colonel John S. Mosby (6 Dec 1833-30 May 1916) and about sixty-nine volunteers set out from Rector's Crossroads in Loudoun County to attack Union pickets near Dranesville, but discovered that the pickets had withdrawn out of reach beyond Difficult Run. They returned down Leesburg Pike and encamped at about 10:00 PM at Miskel's Farm, near where Broad Run emptied into the Potomac, north-east of Leesburg. The farm had belonged to George Miskel (abt. 1818-1860) and his wife before passing to a new owner after their death. Mosby and a few others slept in the farmhouse, and most of the men slept in the barn loft, with the exception of Richard "Dick" Moran (1814-1869), who had left the group to spend the night with a personal friend named Green. Miskel's Farm was surrounded by two fences: an outer fence enclosing the cultivated fields, and an inner fence surrounding the barnyard. Mosby could easily be trapped if attacked, but as far as he knew the closest enemy was eighteen miles away, and Miskel's Farm was the only place he could be sure of obtaining feed for his horses.

A Union sympathizer saw Mosby's men that afternoon and sent word to the Union lines across Difficult Run. Captain Henry Flint (?-1 April 1863) of the First Vermont Cavalry set out with two squadrons to surprise Mosby. On their way down Leesburg Pike, Flint and his men stopped briefly at Green's farm, where Dick Moran was staying. As soon as Flint and his men moved on, Moran galloped off cross-country to warn Mosby. About sunrise Moran raced into the barnyard and shouted a warning just as Flint's first squadron entered through the gate in the outer fence.

Initially, the Federals had the element of surprise and the advantage of better weapons, especially while Mosby's men were trying to catch and saddle their horses. The advantage shifted to Mosby's side, however, once he and his men were mounted and could use their pistols and sabers in the barnyard. Captain Flint and two of his Lieutenants were killed, and Mosby's men drove the Federals back until they were jammed against the outer gate, which they had confidently barricaded behind themselves. Eventually it gave way under the sheer weight of their panic as Mosby's men poured fire into them, and the survivors scattered into the woods and down the road, pursued by Mosby and his men.

Overall the battle was a draw. Mosby allowed himself to be surprised in a narrow place by a superior force, but escaped with few casualties. Flint had the element of surprise and statistically should have won, but making a frontal assault was a mistake. Once he was killed, his leaderless men changed from the trappers to the trapped.

About May 30, 1863 Mosby encountered the First Vermont again. He had just captured and destroyed a train on the Virginia and Alexandra Railroad with theaid of a howitzer when he realized that Federals were quickly approaching. Eventually he had to abandon the gun in order to escape, but, in Mosby's words, he "resolved to make them pay for it as dearly as possible" by raking the enemy repeatedly with grape shot as, once again, they came marching up in a frontal assault.