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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 George Washington, 1st President of the United States, for instance, spent his early youth on the frontier at and beyond Winchester, surveying for Thomas, Lord Fairfax Thomas Fairfax, 6th Lord Fairfax of Cameron. He began his political career by being elected to the House of Burgesses from Winchester.
Colonel James Wood Col. James Wood 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 Gov. James Wood, was Governor of Virginia from 1796 to 1799.
Governor Wood's younger brother, Robert Wood Robert Wood , 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 William McKinley, 25th President of the USA, 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 Captain Thomas Bolling Byrd, Sen. Harry Flood Byrd Governor Harry Flood Byrd, Sr., and, most of all, Admiral Richard E. Byrd Rear Admiral Richard Evelyn Byrd, Jr..
Sen. Byrd's son, Harry Flood Byrd, Jr. Senator Harry Flood Byrd, Jr. , was a complete chip off the old block.
Actress Greer Garson came to Winchester on a war bond tour in 1942, receiving a "key to the city" and generally being feted like an Apple Blossom Queen (the festival was suspended 1942-1945 due to World War II).
To this day the annual Shenandoah Apple Blossom Festival http://thebloom.com/ continues to bring celebrities to Winchester for the festivities. These have included:
- Fleet Adm. Chester W. Nimitz, USN (1946 Minister of the Crown)
- Bing Crosby (1949 Grand Marshal)
- Vice President Alben W. Barkley (1949 and 1950 Minister of the Crown)
- Bob Hope (1949 and 1975 Grand Marshal)
- Van Johnson (1950 Grand Marshal)
- Gen. George Marshall (1951 Minister of the Crown)
- Howard Keel (1952 Grand Marshal)
- Kathryn Eisenhower (niece of President Dwight D. Eisenhower; 1953 Queen Shenandoah)
- Arthur Godfrey (1953 Grand Marshal)
- William "Hopalong Cassidy" Boyd (1953 celebrity guest, "in persona" the whole time)
- Ed Sullivan (1954 Grand Marshal)
- Al "Captain Video" Hodge (1955 Grand Marshal, "in persona" the whole time)
- Winchester's own Patsy Cline (1955-1957 celebrity guest)
- Bert Parks (1956 Grand Marshal)
- Cyd Charisse (1956 celebrity guest)
- James Cagney (1957 Grand Marshal)
- Rep. Sam Rayburn, Speaker of the House (1958 Minister of the Crown)
- Ted Mack (1958 Grand Marshal)
- Gene Barry (1959 Grand Marshal; in persona as "Bat Masterson"; also Grand Marshal in 1961)
- Russ Tamblyn (1959 Firefighters' Marshal)
- Tom Tryon (1960 Grand Marshal)
- President Lyndon B. Johnson (1964 Minister of the Crown because - )
- Luci Baines Johnson (1964 Queen Shenandoah)
- Lucille Ball (1964 Grand Marshal)
- The Carter Family (1964 celebrity guests)
- Jack Dempsey (1965 Grand Marshal)
- Staff Sgt. Barry Sadler, "The Green Berets" (1966 Grand Marshal)
- Willie Nelson (1966 celebrity guest)
- Fran Tarkenton (1968 Sports Marshal)
- Ed McMahon (1969 (Grand Marshal)
- Dizzy Dean (1969 Sports Marshal)
- Astronaut Wally Shirra (1970 Grand Marshal)
- Jesse Owens (1970 co-Sports Marshal)
- Astronaut Alan Shepard (1971 Minister of the Crown)
- Juliana Shepard (Alan Shepard's daughter, 1971 Queen Shenandoah)
- Billy Graham (1972 Grand Marshal)
- Howard Cosell (1972 co-Sports Marshal)
- Mike Douglas (1973 Grand Marshal)
- Frank Gifford (1974 Grand Marshal)
- President Gerald Ford (1975 Minister of the Crown)
- Susan Elizabeth Ford (1975 Queen Shenandoah)
- Col. Harland Sanders (1975-1977 celebrity guest)
- Mickey Mantle (1976 Grand Marshal)
- Elizabeth Taylor & Senator John Warner (1977 co-Ministers of the Crown)
- Sugar Ray Leonard (1977 celebrity guest)
- Dolly Parton (1978 celebrity guest)
- Jack Valenti (1978 celebrity guest)
- Johnny Unitas (1978 celebrity guest)
- Jose Ferrer (1979 Minister of the Crown)
- Maria Ferrer (his daughter, 1979 Queen Shenandoah)
- Jimmy Dean (Grand Marshal)
- Brooks Robinson (1979 co-Sports Marshal)
- Hank Aaron (1980 Sports Marshal)
- Hal Linden (1981 and 1986 Minister of the Crown - crowned *two* daughters)
- Lou Brock (1981 celebrity guest)
- Willie Mays (1984 Grand Marshal)
- Gov. Charles S. Robb (Minister of the Crown 1982, 1983, 1985)
- Greg Louganis (1987 Sports Marshal)
- Press Secretary James Brady (198 Honorary Firefighters' Marshal)
- Gary Coleman (1988 Firefighters' Marshal)
- Olympic bronze medalists Jill Watson & Peter Oppegard (1988 celebrity guests)
- Jill St. John (1989 Grand Marshal)
- Jerry "The Beaver" Mathers (1990 Grand Marshal *and* Minister of the Crown)
- Joan Rivers (1990 celebrity guest)
- Hal Holbrook (1991 and 1992 Minister of the Crown)
- Eve Holbrook (his daughter, 1991 Queen Shenandoah)
- Bob Feller (1991 Sports Marshal)
- Willard Scott (1992 Grand Marshal)
- Frank Robinson (1992 celebrity guest)
- Mary Tyler Moore (1993 Grand Marshal)
- Katie Couric (1994 Grand Marshal)
- Adam "Batman" West (1995 Minister of the Crown *and* Grand Marshal - NOT in persona)
- Sen. Charles Robb (Minister of the Crown for the *fourth* time, 1998)
- Dan Aykroyd (1999 and 2002 co-Grand Marshal, with wife Donna Dixon)
- Pat Boone (1999 celebrity guest)
- Diahann Carroll (2000 Grand Marshal)
- Bobby Allison (2003 Sports Marshal)
- Chevy Chase (2004 Minister of the Crown)
- Cydney Cathalene Chase (his daughter, 2004 Queen Shenandoah)
- Loni Anderson (2004 co-Grand Marshal)
- Sean Astin (2004 co-Grand Marshal, 2014 Minister of the Crown)
- Jackie Joyner-Kersee (2004 Sports Marshal)
- Whitey Ford (2004 celebrity guest)
- Kirk Cameron (2004 celebrity guest)
- Larry " J.R." Hagman (2005 Grand Marshal)
- Dorothy Hamill (2006 Minister of the Crown)
- Alexandra Hamill Forsythe (her daughter, 2006 Queen Shenandoah)
- Johnny Bench (2006 co-Sports Marshal)
- Wayne Newton (2007 Grand Marshal)
A more complete list can be found here: http://thebloom.com/celebrities/