Upperville is sometimes called the town that is “a mile long and an inch wide” because most of the homes line Columbia Street, as Route 50 was called on the original plat.

In the 1760s, young George Washington surveyed much of the area west of Middleburg and bought a tract with a stone house that operates today as the Blackthorne Inn & Restaurant. By 1790, Josephus Carr had assembled 177 acres along Pantherskin Creek, where he established a village of 50 lots called “Carrstown.” Founded in 1797, Carrstown was renamed Upperville, for reasons still unknown, by the 1818-1819 Virginia General Assembly. Like Aldie, Upperville thrived because of its location near a creek that could turn millstones for grinding corn and wheat.

Of the seventy-five buildings that comprised the town in 1976 when it was placed on the National Register, approximated fifty are nineteenth century and well over half of these date prior to 1860.

Several of the earliest houses are stone, such as the Joseph Carr House and Dr. Smith House. The town structures are simple adaptations of their sophisticated counterparts in more urban centers such as Alexandria and Georgetown.

One of the town focal points is the Trinity Episcopal Church, a circa 1950s French Medieval Style building in local sandstone, complimented by a rectory and parish house.

Upperville is the home of the country’s oldest horse shows founded in 1853 by Richard Henry Dulany of nearby Welbourne. On the outskirts of town there is the Piedmont Point-to Point, which is located on a track dating to 1760.

Oakley Farm, one of Upperville’s most historic places, was the scene of two Civil War battles. Ida Dulaney, the owner of Oakley during the war, recalls in her diary that she stood on her balcony watching the armies charge and countercharge through her grounds. The balcony at Oakley still overlooks those same fields which remain unchanged.

The town’s oldest church, the United Methodist Church, begun in 1832, is a notable example of rural Federal style architecture and was used in the Civil War as a Union Hospital. On June 21, 1863 10,000 cavalry and infantry clashed here in The Battle of Upperville.

Union cavalry made a determined effort to pierce Stuart’s cavalry screen. Hampton’s and Robertson’s brigades made a stand at Goose Creek, west of  Middleburg, and beat back Gregg’s division. Buford’s column detoured to attack the Confederate left flank near Upperville but encountered William E. “Grumble” Jones and John R. Chambliss brigades while J.I. Gregg’s and Kilpatrick’s brigades advanced on. After furious mounted fighting, Stuart withdrew to take a strong defensive position in Ashby Gap.

After furious mounted fighting, Stuart withdrew to take a strong defensive position in Ashby Gap, even as Confederate infantry crossed the Potomac into Maryland. As cavalry skirmishing diminished, Stuart made the fateful decision to strike east and make a circuit of the Union army as it marched toward Gettysburg. There were 400 total casualties.

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