The physical and psychological heart of Northern Virginia’s hunt country, Middleburg is a compact and fastidious village retaining the qualities of its early years. Founded in 1787 by Leven Powell, a Revolutionary War officer and regional Federalist leader, the town developed as a coach stop and relay station on Ashby’s Gap Turnpike, becoming by the mid-19th-century a commercial center for lower Loudoun and upper Fauquier counties. The town saw frequent Civil War cavalry action and won a reputation for fierce Confederate loyalty but afterwards it declined in fortune and population. By the second decade of the 20th century, it assumed a new identity as a social and equestrian center. With its tree-lined streets, brick sidewalks, and harmonious scale, the town has a diverse collection of late-18th- to early-20th-century architectural styles highlighted by early stone and brick structures.