Just 20 miles from Washington, D.C.’s Dulles Airport and 40 miles from the Nation’s Capital, Middleburg has an enviable position of being easily accessible to so many visitors while being able to protect its authenticity, history and culture.
Middleburg was established in 1787 by American Revolutionary War Lieutenant Colonel and Virginia statesman, John Leven Powell. He purchased the land for Middleburg at $3.50 per acre from Joseph Chinn, a first cousin of George Washington. It had been called "Chinn's Crossroads", and was then called Powell Town. When Leven Powell declined to have the town named after him, the town was called Middleburgh, and later, simply Middleburg. The village is located midway between the port of Alexandria and Winchester, Virginia, on the Ashby Gap trading route (now followed by U.S. Route 50).
In 1863, Middleburg witnessed two skirmishes during the Gettysburg Campaign of the Civil War, giving it a place in that important historical period.
From the early 1900s, Middleburg began welcoming visitors who participated in foxhunting and steeplechasing. The village soon earned a reputation as the "Nation's Horse and Hunt Capital", attracting prominent visitors from across the U.S. Middleburg is the home of the National Sporting Library research center for horse and field sports and its recently opened art gallery and museum.
In 1961, civil rights activists pressed John F. Kennedy on local segregation issues during his residency outside town. His wife, Jacqueline Kennedy (an avid equestrian), and their children were pictured riding on Pamela Harriman’s estate during his time in office.
The Middleburg Historic District, comprising the 19th-century center of town, is listed on the National Register of Historic Places, as is the Red Fox Inn, the oldest building in town, and billed as the oldest continually operated inn in the U.S.
Middleburg was recognized in 2008 for its historic preservation efforts by being designated a Preserve America Community by then-First Lady Laura Bush.
The Mystique of Middleburg and its surrounding estates have captivated many well-known personalities from the Kennedys, Elizabeth Taylor, Robert Wagner, and Oliver North - all of whom have called Middleburg home. A peek behind the grand stone entrances of massive estates with names such as "The Meadows" or "Heathfield" that belong to families such as the Firestones, Mellons, and Marriotts, attending one of the numerous equestrian events in the area, including the oldest horse show in the Country, or spending a day touring any of the nearby 30+ wineries allows visitors a chance to understand just a little of the gracious equestrian and country lifestyle that residents have come to treasure.