Middleburg: Hunt Country's Capital Town

Middleburg was established in seventeen eighty-seven, platted by Leven Powell on land that had been a tavern stop halfway between Alexandria and Winchester on the old Ashby's Gap Turnpike. It became the social center of Virginia's Hunt Country, the piedmont landscape where wealthy Washingtonians have kept horses, foxhunted, and built estates for over a century. During the Civil War, Confederate cavalry commander J.

E.B. Stuart made Middleburg his headquarters, and Union and Confederate forces fought through the village more than once in eighteen sixty-three.

Jacqueline Bouvier Kennedy had a personal connection to the area, and the town became briefly famous again when the Kennedy family kept a retreat nearby. Today Middleburg, with fewer than a thousand permanent residents, supports high-end equestrian boutiques, wine country tourism, and a historic Main Street little changed since the eighteen hundreds.