Middleburg was founded in 1787 and its history is indeed an interesting one. Revolutionary War Lieutenant Colonel and Virginia Statesman Levin Powell purchased land known as “Chinn’s Crossroads” for $2.50 an acre from Joseph Chinn, first cousin to George Washington. Powell changed the name to “Middleburg” because of the town’s location halfway between Alexandria and Winchester on the Ashby Gap trading route, which is now Route 50.
Today’s Middleburg is a charming town filled with eclectic shops, quaint little art galleries and nearby wineries. Take an afternoon and stroll the excellent shoppes in town such as Duchessa of Middleburg, Lou Lou, Christmas Sleigh, Highcliffe Clothiers, Betsey, English Country Classics, Fun Shop, Créme de la Créme and Wylie Wagg. Browse the town’s antique stores including Hastening Antiques and Middleburg Antique Emporium. Check out the latest exhibits at Trowbridge-Lewis Galleries and Byrne Gallery. Plan a visit to one of the Virginia wineries such as Stone Tower Winery, Barrel Oak Winery, Boxwood Winery, Chrysalis Vineyards and Three Fox Vineyards. And then stop by the National Sporting Library dedicated to horse and field sports.
There are always things to do in Middleburg Va! The Middleburg Spring Races in Glenwood Park is an exciting event each year and a fundraiser for INOVA Loudoun Hospital and other charities. The Virginia Fall Races also held at Glenwood Park benefit INOVA Loudoun Healthcare Foundation. On the first Saturday of December, the town celebrates “Christmas in Middleburg” with parades, festivities . . . and even a Middleburg Wine Crawl!