It's rather surprising how many persons of note were born in, lived in, or had something significant happen while visiting Winchester, VA. It's not just the city's many Civil War connections - it started long before that, and continued long afterward.
George Washington http://www.geni.com/people/George-Washington-1st-President-of-the-USA/6000000008211776777, for instance, spent his early youth on the frontier at and beyond Winchester, surveying for Thomas, Lord Fairfax http://www.geni.com/people/Thomas-Fairfax-6th-Lord-Fairfax-of-Cameron/6000000012954375714. He began his political career by being elected to the House of Burgesses from Winchester.
Colonel James Wood http://www.geni.com/people/Col-James-Wood/6000000001948207018 was chiefly responsible for laying out the town of Winchester, and probably gave it its permanent name (after his birthplace of Winchester, England).
His son, James Wood II http://www.geni.com/people/Gov-James-Wood/6000000018369418927, was Governor of Virginia from 1796 to 1799.
Governor Wood's younger brother, Robert Wood http://www.geni.com/people/Robert-Wood/6000000001948006586 , was the person most responsible for the construction of "Glen Burnie", the Wood/Glass family showplace in Winchester, VA.
The Civil War produced some usual and unusual suspects: not only the usual Generals, including Jackson and Early on the Confederate side, and Sheridan and the notorious Milroy on the Union side, but also some "lesser" lights who went on to bigger things, and a coterie of women who left diaries preserving their (often acerbic) observations about the impact of the Civil War on the town.
William McKinley http://www.geni.com/people/William-McKinley-25th-President-of-the-USA/6000000008127235311, later President of the United States, was inducted into the Masons while on active duty in occupied Winchester. The house where this occurred is long gone, but the local Lodge remembers.
Three brothers from Winchester had a significant impact on Virginia and US history in the 20th century: Thomas Bolling Byrd http://www.geni.com/people/Thomas-Byrd/6000000022148806377, Sen. Henry Flood Byrd http://www.geni.com/people/Harry-F-Byrd-Sr-US-Senator/6000000010496622697, and, most of all, Admiral Richard E. Byrd http://www.geni.com/people/Rear-Adm-Richard-E-Byrd-Jr-Polar-Explorer/6000000010524688686.
Sen. Byrd's son, Harry Flood Byrd, Jr. http://www.geni.com/people/Harry-F-Byrd-Jr-U-S-Senator/6000000010524850182 , was a complete chip off the old block.
To this day the annual Shenandoah Apple Blossom Festival http://thebloom.com/ continues to bring celebrities to Winchester for the festivities.