Middleburg was involved in the Civil War as troops from both Union and Confederate armies camped and skirmished here on their way to Gettysburg. Confederate Colonel John S. Mosby used Middleburg for a time as a base camp from which to raid the region, and Route 50 is named after him (John Mosby Highway). Today there are approximately 600 people currently residing in the town established in 1787 by Revolutionary War Lieutenant Colonel and Virginia statesman, Levin Powell. He purchased the land for Middleburg at $2.50 an acre from Joseph Chinn, first cousin to George Washington. Previously called "Chinn's Crossroads," Powell chose the name Middleburg because of the town's location midway between Alexandria and Winchester on the Ashby Gap trading route (now Route 50).

Since the 1730s, Middleburg had been a staging point for weary travelers along the Ashby Gap Road. The legacy of the colonial era continues today at Middleburg's charming inns that provide first rate accommodations to visitors from around the world. The Red Fox Tavern, billed as the "oldest original inn in America" was a meeting spot for Confederate Colonel John Mosby and his Rangers. A century later, President Kennedy's press secretary, Pierre Salinger, held press conferences at the Red Fox in the Jeb Stuart room.

Today, Middleburg is the nation's horse and hunt capital. It is home to many horses and equestrians, including many of the nation's Olympic equine competitors. Foxhunting, steeplechase racing, boots, breeches, and horse trailers are common topics of discussion. The horse theme carries through Middleburg's retail establishments with names such as the Coach Stop Restaurant, Finicky Filly, and Cuppa Giddyup. Middleburg offers a wide array of unique shopping from tack stores, art galleries, antique stores, and specialty shops.

Celebrity sightings of such local residents as Robert Duvall or Willard Scott have been known to occur at the Safeway grocery store in the center of town, one of the few Safeways in the nation with chandeliers. Past residents have included John and Jackie Kennedy, Elizabeth Taylor, and Pamela Harriman, the former Ambassador to France. Now the region is home to many Fortune 500 CEOs and heirs. In spite of the wealth and celebrity that reside here, the town maintains a distinct charm and the residents a down to earth attitude.

Annual Middleburg events include the Hunt County Stable Tour held on Memorial Day weekend when more than a dozen major horse properties and equine facilities open their doors to the public, and the annual Christmas Parade on the first Saturday in December which is led by the local hunt in their red ("pink") hunting jackets on horses followed by hounds.

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