The Journey Through Hallowed Ground

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Middleburg, VA


If there was an official capital of horse country in America, it would be Middleburg. This small town of about 600 residents has held undisputed claim to this title since the early 20th century when wealthy sporting enthusiasts and their horses and hounds claimed the town and its lush rolling countryside as their own.  Celebrities, statesmen, writers, members of the jet set, and Olympic-caliber horseback riders have rubbed elbows in Middleburg, including the late philanthropist and sportsman Paul Mellon, President and Mrs. John F. Kennedy, and F. Scott Fitzgerald. 

Middleburg has a rich Civil War history. It was one site in a series of cavalry clashes in 1863 during Lee’s march to Gettysburg (along with Upperville and Aldie). John Mosby, the “Gray Ghost” of the Confederacy, used Middleburg as a base of operations and hide out on many of his daring raids on Federal supply lines. 

Middleburg was so named because it was midway on the Winchester-to-Alexandria trading route known as the Ashby Gap Road, which is now Route 50. Middleburg's historic architecture, tree-lined streets, and refined sophistication are its main attractions. Perusing Middleburg's charming shops and unique dining establishments, whose names carry the town's horse country theme, is the main activity. 

Annual Middleburg events include the Hunt County Stable Tour held on Memorial Day weekend when more than a dozen private horse estates and equine facilities open their doors to the public, and the annual Christmas Parade on the first Saturday in December which features traditional marching bands, floats, and even Santa, and is led by the hounds of the local hunt followed by horseback riders in their red ("pink") hunting jackets. (sources: and

Directions to:

Local Tourism Resources:

  • Visit Loudoun and Loudoun County Visitors Center
    Market Station 112-G South St. SE
    Leesburg, VA 20175
    703-771-2170 ext. 11 or 800-752-6118 ext. 11
    Daily 9:00 am - 5:00 pm / Closed Thanksgiving, Christmas, and New Year's Days
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