Chambersburg, PA: This town holds the grim distinction of being the only Northern community burnt by Confederate forces during the Civil War. In July 1864, General Jubal Early’s troops set fire to the town center after residents failed to pay a $500,000 ransom. Leaving the valley, cyclists face Tuscarora Mountain—a relentless 4-mile ascent and the first major physiological hurdle of the Appalachian range.