Heavy rain continued to fall at 6 a.m. as the regiments of the 1st Brigade fell into the line of march, with the 22nd Massachusetts in the lead. The Brigade marched through Utica and Creagerstown, and then began the long climb toward the summit of the High Knob of the Catoctin Mountains, sloshing through streams of rainwater from the surrounding heights as it raced across their path and toward the valley below. Reaching the summit around 10 a.m., the brigade was enveloped in darkness and cloud cover that seemed to almost rest on the tops of their heads. Overhead, quick successive lightening strikes illuminated the sky, while thunder rolled incessantly, as if the Gods were rolling strike after strike in a game of ten pins Toward the halfway point, of what was now a downhill trek, the sun broke through bathing “grainfields everywhere in alternative stripes of green and yellow.”
After completing a 15 mile march that brought them to the floor of the Valley of Frederick, the Brigade was called to a halt for the day at one o’clock in the afternoon, just short of Middletown. Later in the afternoon, while men took the time to eat rations that had been distributed among the ranks and dried their clothes, the distant sound of cannonading could be heard in the direction of Boonsboro, seven miles away. What they couldn't hear were the hoofbeats, the rattle of sabres, and the crackling sound of carbines and pistols as two opposing cavalries clashed.