The town where history is measured in horseflesh and heritage

Countries & Cities · Published 12 October 2026 Swipe more like this →

In short: Middleburg, Virginia, is more than a quiet town; it is a curated landscape of 18th-century estates and elite equestrian culture. From its origins as a Revolutionary War land purchase to its status as a national hub for foxhunting, the town serves as a living museum of American rural prestige.

Established in 1787 by Revolutionary War officer Leven Powell, Middleburg was born from a land purchase made in 1763. The land was bought for $2.50 per acre from Joseph Chinn, a first cousin of George Washington. Originally known as 'Chinn's Crossroads' and later 'Powell Town,' the community eventually settled on the name Middleburg after Powell declined to have the town named in his honor.

Its location was strategically significant, situated midway between the port of Alexandria and Winchester on the Ashby Gap trading route. The town’s identity is inextricably linked to the 'Nation's Horse and Hunt Capital' moniker, a reputation solidified in the early 1900s. This era saw a surge of visitors drawn to the region for foxhunting and steeplechasing, attracting prominent figures from across the United States.

Today, this legacy is anchored by the 15,000-square-foot National Sporting Library research center, which serves as a primary repository for horse and field sports history. Beyond its sporting fame, Middleburg preserves deep historical layers. Claiming to be the oldest inn still running in the U.S., the Red Fox Inn & Tavern first opened in 1728 under the name 'Chinn's Ordinary'. The town also served as a site of conflict during the Civil War, witnessing two skirmishes during the Gettysburg campaign in 1863. In the 20th century, it became a site of political significance when John F. Kennedy and Jacqueline Kennedy rented Glen Ora in 1961, during which time they were pressured by Civil Rights activists regarding local segregation.

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