Skip to main content

Get to know Middleburg

Established in 1787, Middleburg was previously called Chinn’s Crossroads, though it was renamed to emphasize its location midway between the port of Alexandria and the many factories of Winchester. Renowned as the heart of Virginia’s Hunt Country, the storied town became a popular destination for fox hunting and steeplechasing by the turn of the last century and plays host to a variety of equestrian events throughout the year, the best known being the Middleburg Spring Races. Today, Middleburg is also a destination for the arts, with draws like the annual Middleburg Film Festival. Numerous old estates in Middleburg include Glen Ora, the famed country retreat of President Kennedy. Early American spirit is alive and well in Middleburg’s downtown, filled with old inns, charming shops, and eclectic eateries. You can still have a pint at the Red Fox Inn & Tavern, established by Joseph Chinn way back in 1728.

Nearby Neighborhoods:

Living in Virginia Hunt Country

Virginia Hunt Country is a land of rolling hills and stacked stone walls, punctuated with the sights and sounds of troops of horses galloping, with riders astride in the traditional uniform of red coats and black helmets. This swath of countryside does not have definitive borders, but is generally considered to stretch over Loudon, Fauquier, and Rappahannock Counties. Depending on who you ask, the region’s boundaries may extend into nearby counties, but everyone agrees that Hunt Country is centered on Middleburg, a small hamlet of less than 1,000 people. The idea of porous borders extends to the landowners here, with farm and estate owners often including provisos on deeds that the riders (and hikers) be allowed to cross their land freely when traversing the verdant terrain. Estates can include considerable acreage and baronial houses, but the vibe in the local villages is low-key and casual, while offering some outstanding dining and shopping experiences.