During the Revolutionary War, the Virginia House of Burgesses chose local resident and French and Indian War veteran Daniel Morgan to raise a company of militia to support General George Washington's efforts during the Siege of Boston. He led the 96 men of "Morgan's Sharpshooters" from Winchester on July 14, 1775, and marched to Boston in 21 days. Morgan, Wood, and others also performed various duties in holding captured prisoners of war, particularly Hessian soldiers.
Hessian soldiers were known to walk to the high ridge north and west of town, where they could purchase and eat apple pies made by the Quakers. The ridge became affectionately known as Apple Pie Ridge. The Ridge Road built before 1751 leading north from town was renamed Apple Pie Ridge Road. The local farmers found booming business in feeding the Virginia Militia and fledgling volunteer American army.
Following the war, the town's first newspapers, The Gazette and The Centinel, were established. Daniel Morgan continued his public service, being elected to one term in the U.S. House of Representatives (1797–1799).
Winchester and the surrounding area were the site of numerous battles during the American
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