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Middleburg (and Upperville)

A Little History

Sitting on the southern border of Loudoun County, next to Fauquier County, Middleburg was originally called “Chinn’s Crossroads”, and was officially established in 1787.  Middleburg was named so because it’s the halfway point between Alexandria and Winchester along Route 50!

But, starting in the early 1900s it became known for its fox hunts and steeplechase horse racing.  It quickly earned the reputation as the “Nation’s Horse & Hunt Capital”!  This heritage is still on display today, most prominently during the town’s annual Christmas Parade where dozens of horses and hounds make their way through town.

In this video you can see our Middleburg Office behind the riders!

Historic Middleburg Real Estate

The Lifestyle & Amenities

Glenwood Park is still host to three large horse events, the Middleburg Spring Races, the Point to Point races, and the Fall Races.  And you’ll find one of America’s oldest horse shows at the neighboring town of Upperville (just west of Middleburg), the Upperville Colt & Horse Show!

They also play host to the Middleburg Film Festival here!  Middleburg may be a small town, but this four day Film Festival attracts BIG stars and movies!  In 2023, they featured Oscar nominated movies as “American Fiction” (starring Jeffrey Wright), “Anatomy of a Fall” (Canne’s Film Festival Palme D’or winner), The Holdovers (Paul Giamatti), Saltburn (Barry Keoghan & Margo Robbie), Nyad (Annette Bening & Jodie Foster), “Zone of Interest” (Canne’s Grand Prix winner) and many others.  The event draws in major actors, directors and producers from around the world!

They also play host to the Middleburg Film Festival here!  Middleburg may be a small town, but this four day Film Festival attracts BIG stars and movies!  In 2023, they featured Oscar nominated movies as “American Fiction” (starring Jeffrey Wright), “Anatomy of a Fall” (Canne’s Film Festival Palme D’or winner), The Holdovers (Paul Giamatti), Saltburn (Barry Keoghan & Margo Robbie), Nyad (Annette Bening & Jodie Foster), “Zone of Interest” (Canne’s Grand Prix winner) and many others.  The event draws in major actors, directors and producers from around the world!

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