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 15,000-square-foot (1,400 m2) National Sporting Library research center for horse and field sports, which publishes Thoroughbred Heritage on the Internet. A new addition is being made to include an art gallery and museum.
The Middleburg Historic District, comprising the 19th-century center of town, is listed on the National Register of Historic Places. The oldest building in town, the Red Fox Inn, was originally established in 1728 by Joseph Chinn as Chinn's Ordinary and is billed as the oldest continually operated inn in the U.S.
Middleburg was named as the location of the mysterious crop circles in the horror film spoof Scary Movie 3 (2003). The film shows an actual map of the Middleburg area, complete with actual surrounding towns and Route 15 pictured on the map.