Confederate General Richard Ewell's Second Corps had been ordered to clear the Shenandoah Valley for the advance of the Army of Northern Virginia into Pennsylvania. The main obstacle was the heavily fortified Union occupied town of Winchester, Virginia, garrisoned by Robert H. Milroy's division of around 7000 men. Milroy's confidence in his formidable defenses was not borne out and despite an attempt to break out, much of his division was captured. The comprehensive defeat caused panic in the North and Lee's road to Pennsylvania was now open. (By John Osborne)
The steamer Maple Leaf was chartered to transport 97 Confederate prisoners of war, mostly officers, from Fort Monroe to imprisonment at Fort Delawarenear Wilmington. Just two hours into the voyage, the prisoners overpowered their guard and ran the vessel ashore near Cape Henry. Sixty of them made for the Virginia shore and freedom in the Maple Leaf's boats. The charter then was refloated and turned back to Fort Monroe with the remaining prisoners and arrived the next day. (By John Osborne)