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Village of Middleburg The town of Middleburg was established in 1787, the population of people residing in town is approximently 600. In 1787, during the Revolutionary War, Lieutenant Colonel an Virginia statesman Levin Powell purchased the land for Middleburg at $2.50 per acre by Joseph Chinn. Chinn, first cousin to George Washington previously called the town "Chinn's Crossroads", Powell renamed the town which is now called Middleburg due to the town's location between Winchester and Alexandria on the Ashby Gap trading route, which is now called Route 50. Since the 1700's, Middleburg has been a meeting point for travelers along the Ashby Gap Road. The colonial era continues in Middleburg with charming inns that provide first rate accomondations from all around the world today. There are several inns within the town limits, including historic Red Fox Inn and Tavern, "the oldest original inn in America," Confederate Colonel John Mosby and his Rangers used to meet at the Red Fox Tavern and a century later, President Kennedy's press secretary, Pierre Salinger, held press conferences at the Red Fox in the Jeb Stuart room. Located across the street is the historic Windsor House Inn, circa 1824. Catherine Broun ran this inn which during the Cival War was known as the Colonial Inn. Catherine served meals to Union troops for several years including when they occupied Middleburg in 1862, even though she sympathized with the south. In the 1900's, the charming village earned a reputation as the "Nation's Horse and Hunt capitol," attracting new visitors for foxhunting and steeplechasing from all over the United States. For more than 250 years, Middleburg has been a host community and at no surprise has developed high concentration of fine inns, shops and restaurants.
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