Adding insult to injury, the defeated Confederate Army of Northern Virginia was pounded by rain as it withdrew from Gettysburg. The weary men marched over twelve hours through the muddy mountain passes into Maryland. Around sunrise on July 5, 1863, the 1st Vermont Cavalry Regiment rode into Leitersburg, Maryland and saw the Confederate wagon train ambling through town. Its wagons overflowed with wounded soldiers. The Vermonters dashed into their midst, spoiling for a fight, but the Southern teamsters mostly gave up without a fight. They rode away with around 100 prisoners and destroyed as many wagons as they could before withdrawing.

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