In the fight Mosby and his men displayed many characteristics that would become their hallmark including the attack on numerically superior force while inflicting disproportionate casualties to those received.

Stuart dispatched his scout John S. Mosby and 15 of his cavaliers to the lower Loudoun Valley in Fauquier County to conduct operations against Union forces occupying Northern Virginia.

On January 28, the small band met at Mount Zion church, 0.5 miles (0.80 km) east of Aldie and set on their first raid against Federals in Chantilly.

On March 2, in response to the raids, Colonel Sir Percy Wyndham dispatched 200 troopers of the 18th Pennsylvania under Major Joseph Gilmore from Fairfax towards Middleburg to find and capture Mosby and his men.

In the town, the Union force, many of whom were reportedly drunk, began searching local residences and arresting citizens in an attempt to smoke out Mosby's men.