Shortly after Confederate Second Corps commander Lt. Gen. Richard S. Ewell swept Maj. Gen. Robert H. Milroy away from Winchester, Virginia, Brig. Gen. Benjamin Franklin Kelley, the last functional Union commander in that sector, ordered his men to converge on New Creek to protect the B&O Railroad. This left the border town of Cumberland, Maryland unoccupied. Into that vacuum rode Confederate Brig. Gen. John D. Imboden and his cavalry brigade. At dawn on June 17, 1863, the 18th Virginia Cavalry Regiment appeared on the hills overlooking the town and demanded its surrender. The undefended town had little choice but to comply. Damage was minimal. The cavaliers bought supplies with worthless Confederate money and destroyed the telegraph station before moving on.

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