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Just days later, they held the first Virginia Gold Gup race. From its beginning, the race was intended to be a national event drawing “the best hunters in America.” Unlike today’s sevenrace card, that first Virginia Gold Cup was a single-race event, riders to be “gentlemen wearing racing colors or officers of the U.S. Army in uniform.” Nine horses competed that May at Oakwood, the great estate of Hugh Ramey on Waterloo Road near Warrenton overlooking the Blue Ridge Mountains once owned by President Lincoln’s personal physician, Dr. Gary Grayson.
The first “Gold Gup” was won by Irish Laddie, owned by the beautiful and vivacious Katherine Hitt of Middleburg and trained and ridden by highly regarded Middleburg horseman Arthur White.
In 1925 Mrs. Hitt, a society belle of the time and daughter of a U.S. Senator, surprised the race organizers by twice more repeating her win with different horses and retiring the first Gold Cup. In all years since, the prestigious cup has been retired only five more times. The current Cold Gup, last won in 1903 in the England Grand National at Aintree, must be won by the same owner five times to retire.
In 1924 the race moved to a new course, Broadview Farm near Warrenton, and was run for the first time under national steeplechasing rules. It has run each year since with few interruptions. The only years in
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