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which the Gup was not run were during World War II, and in 1948 due to a schedule conflict with Maryland’s My Lady’s Manor date.
Although the early years of the Gold Gup were less elaborate and run before smaller crowds than today’s races, most of the essentials have not changed. From the start the Gold Gup has always attracted the nation’s top steeplechase horses and riders. One of the best riders in the 1920’s and ‘30’s was Jack Skinner, a dashing horseman from Middleburg who won the race three times in a row for Mrs. Sumner Pingree of Boston. Mrs. Pingree retired the second challenge trophy in 1933. Her total of four Gold Gup wins were not equaled by any other owner until Saluter, owned by Henry Stem of Richmond, Virginia, swept to six consecutive wins from 1994 to 1999.
It was not unusual in die early years for horses to be entered in both of America’s most challenging timber races, the Maryland Hunt Gup and the Viiginia Gold Gup in the same year, the ultimate steeplechase challenge. These two demanding races over four miles of 4- to 5-foot solid rail fences are scheduled only one week apart; and only one horse, Howard Bruce’s remarkable Billy Barton ridden by Albert Ober, has ever won both races in the same year (1926).
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