Middleburg, Loudoun County, VA
Since the 1730s, the town now known as "Middleburg" had been a staging point for weary travelers along the Ashby Gap Road. In 1787 Revolutionary War Lieutenant Colonel and Virginia statesman, Levin Powell purchased land at that staging point for $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. He carefully subdivided the land into lots and sold them to aspiring businesses and residents. Several inns sprang up within the corporate limits, including the historic Red Fox Inn and Tavern which is now billed as the "oldest original inn in America." The Red Fox Tavern was a meeting spot for Confederate Colonel John Mosby and his Rangers during the Civil War, and a century later, President Kennedy's press secretary, Pierre Salinger, held press conferences at there in the Jeb Stuart room. Across the street from The Red Fox is another gracious reminder of the past, the Windsor House Inn, circa 1824. During the Civil War it was known as the Colonial Inn and was run by Catherine Broun. Although Catherine sympathized with the South, she generously served meals to Union troops at the inn as well when they occupied Middleburg in 1862.
After the turn of the century, Middleburg began welcoming a new wave of visitors that descended on the town for foxhunting and steeplechasing. The charming village soon earned a reputation as the "Nation's Horse and Hunt Capital," attracting prominent visitors from across the United States.
There are approximately 600 people currently residing in (now Route 50). Serving as a host community for more than 250 years, it is no surprise that Middleburg has developed such a high concentration of fine inns, shops and restaurants.
From The History of Middleburg courtesy of the Middleburg OnLine website.