Middleburg was established in 1787 by Leven Powell, one of Virginia's founding fathers.
Following a long decline after the Civil War, the arrival of foxhunting in 1904 gave the town an international reputation for breeding, showing, and racing Thoroughbred horses. Over the ensuing decades, Middleburg would undertake significant historic preservation, but the town would also be remarkable for its laissez-faire attitude toward the rich and famous. Movie stars and presidents were seduced not only by Middleburg's horses, hounds, and history, but also by its respect for the privacy of its more renowned residents and visitors. In Middleburg, photographs from the collections of local residents Howard Allen and Tyler Gore as well as from the National Sporting Library, the Library of Congress, and other sources were chosen to reflect the character and charm of this historic village.