Middleburg (population 650) was founded in 1787 by Leven Powell, a Revolutionary War officer and regional Federalist leader. The land, located at the foot of the Virginia Piedmont, was purchased for $2.50 an acre from Joseph Chinn, a cousin of George Washington. Previously known as Chinn’s Crossroads, the town received its current name from Powell based on its function as a rustic stagecoach stop midway between Alexandria and Winchester.

Much of its early rise can be attributed to the growth of mills and the development of the flour trade. With the formation of the Ashby’s Gap Turnpike Company in 1810, Middleburg became an important stop on a paved road that ran east to west along the lines of today’s Route 50. In the early 1800s, Middleburg had eight places of business, including two taverns. By mid-century, it had become a commercial center for lower Loudoun and upper Fauquier counties.

By the 1920s, Middleburg had assumed a new identity as a social and equestrian center. The town came into prominence in the early 1960s when President John F. Kennedy and his family visited the area for retreats. Since that time, Middleburg has prospered, becoming the nation’s foremost area for fox hunting, thoroughbred breeding, and horse racing.

Today Middleburg is a scenic village that hosts steeplechase races, garden and stable tours, and annual celebrations including Christmas in Middleburg. The Middleburg Hunt’s hounds lead horses and riders in full attire through the historic center of town to kick off the holiday celebration, followed by a parade. The nearby Upperville Colt and Horse Show, the oldest horse show in the country, brings riders from around the nation, and Glenwood Park, a circa 1911 equestrian center, hosts year round activities.

Many historic inns cater to visitors, and other historic buildings are used as boutiques, galleries, and restaurants. More than 160 buildings in Middleburg are listed on the National Register of Historic Places and the Virginia Landmarks Register. The Red Fox Inn and Tavern, a town landmark dating to 1728, still offers dining and lodging.

Middleburg is a Certified Local Government and participates in the Journey Through Hallowed Ground Partnership’s Main Street Initiative. This partnership encourages economic development within the context of historic preservation, and facilitates regional heritage tourism promotion. A Joint Architectural Review Board, with participation from Loudoun County, Middleburg, Leesburg, and Purcellville, recognizes outstanding projects within historic districts and brings attention to the benefits of historic district designation.

Designated a Preserve America Community in November 2008.

For more information

Middleburg - Journey Through Hallowed Ground

Hupp’s Hill Battlefield Park