Date:    June 17 – 19, 1863
Result:    Inconclusive
Troops Engaged:    6,000 US; 7,000 CS
Casualties:    367 US; 40 CS

On June 17, the 1st Rhode Island cavalry was ordered to scout west from Thoroughfare Gap to Middleburg. The Rhode Islanders initially took the town, forcing Stuart and his staff to flee. The 1st Rhode Island Cavalry regiment of less than 300 men, however, was insufficient to hold the town when three Confederate brigades arrived and reoccupied the town. The 1st Rhode Island was routed, losing more than two-thirds of its force killed, wounded, or missing.

As Lee’s infantry continued its march northward, Stuart’s cavalry continued to protect its right flank by occupying the Blue Ridge passes. Elements of Stuart’s and Pleasonton’s forces again engaged in Middleburg on June 19, 1863. The day’s early fighting occurred just west of town at Mount Defiance along the Ashby’s Gap Turnpike. Stuart initially held this position but was pushed back more than one mile to Bittersweet Farm. Both of Stuart’s flanks were threatened during the battle, but the Federals did not push this advantage. Although Pleasonton held the battlefield when the firing ceased, he failed to do serious damage to Stuart or his screening movements.