The Guide to Living in Upperville, Virginia

UPPERVILLE, VIRGINIA

The History of Upperville, Virginia

Located in the heart of Virginia Hunt Country, the historic town of Upperville, Virginia offers the ideals of small town charm along the foothills of the Blue Ridge Mountains.

Established in 1797 by Josephus Carr along the Alexandria-Winchester Turnpike, Upperville, Virginia today is regarded as one of America’s most revered equestrian communities.

Despite its status as one of Virginia’s smallest town, Upperville, Virginia is the birthplace to many iconic Mid-Atlantic and Virginia Hunt Country traditions.

The Upperville Colt & Horse Show, established in 1853 by Richard Henry Dulany, represents the oldest continuously running horse show in the United States.

A designated landmark on the National Register of Historic places, Upperville, Virginia is also home to many of America’s most iconic country homes and estates, including Sandy Lerner’s Ayrshire Farm and Paul and Bunny’s Mellon’s Oak Spring Farm estate as well as a variety of charming 19th-century style brick, wood, and log homes along the upper-end of the town’s main thoroughfare.

Among its most notable architectural structures, Trinity Episcopal Church stands as one of the most significant in Upperville, Virginia. Designed by H. Page Cross in the French medieval parish style, it was donated by philanthropist Paul Mellon in the 1950s.

And for lovers of the outdoors and adventure, Sky Meadows State Park offers access to the Appalachian Trail and stunning vistas of the Blue Ridge Mountains across over 1,000 acres of protected park land.