About 2 pm, Gregg's advance column of the 2nd and 4th New York, 6th Ohio, 1st Maine, 1st Rhode Island, and 1st Massachusetts, under the command of Brig. Gen. Judson Kilpatrick arrived in Aldie. Just west of the village the 1st Massachusetts encountered Munford's pickets and drove them back. Around the same time, the rest of Munford's brigade (the 1st, 4th, and 5th Virginia Cavalry, under the command of Col. Williams Carter Wickham) arrived at Dover Mills, a small hamlet on the Little River west of Aldie. Wickham ordered Col. Thomas L. Rosser to take the 5th Virginia to locate a campsite closer to Aldie. As they moved east they ran into the Massachusetts men and easily drove them back through Aldie to the main Union body. After positioning his sharpshooters (50 men of Company I under Capt. Reuben F. Boston) east of the William Adam farmhouse, Rosser deployed west along a ridge that covered the two roads leading out of Aldie and awaited the arrival of the Federals, as well as Munford and Wickham. As Rosser withdrew west, the 1st Massachusetts, with aid from the 4th New York, charged against what they believed to be a retreat. Rosser's line held and he mounted a countercharge in concert with a sharp volley from the sharpshooters he had placed on his left and easily drove the Federals back, securing his hold on the Ashby's Gap Turnpike.