A linear 1790s turnpike village on the Fauquier–Loudoun line, home of America’s oldest horse show.
History
Upperville was laid out in 1797 by Joseph Carr on about fifty acres along Pantherskin Creek, on the Fauquier County side of the Loudoun line. Carr had settled here years earlier with a stone house and store, and the place was first known as Carrstown before the General Assembly formally established it as Upperville. Carr arranged the village as a single long street, with commerce at the western end and homes to the east.
The village stretched along the turnpike between Alexandria and Winchester, today’s U.S. Route 50, and filled with 19th-century houses of brick, frame and log. On June 21, 1863, Union cavalry under Alfred Pleasonton and J.E.B. Stuart’s Confederates fought here in the Battle of Upperville, an inconclusive clash during the march toward Gettysburg; the 1862 fighting around Unison also reached the area.
In 1853 Richard Henry Dulany founded the Upperville Colt & Horse Show, widely called the oldest in the nation. A century later, Paul Mellon funded Trinity Episcopal Church, built in the style of a medieval French parish church and now a community landmark.
Courses through Upperville
Rides through Upperville
- Wrapping up a 306 mile weekMay 27, 2013 · 38.1 mi
- Lunch at Hunter’s Head TavernJun 22, 2013 · 44.6 mi
- Upperville gravely loopsNov 26, 2022 · 34.4 mi
- Upperville, Heavenly LoCo gravel rideJul 4, 2023 · 24.3 mi
- Rare road cycling ride: Lunch in UppervilleJul 27, 2025 · 30.9 mi
- Upperville – Delaplane Friday loopAug 7, 2026 · 20.2 mi
From our rides near Upperville
Sources: Virginia DHR – Upperville Historic District (030-5438) · Wikipedia – Upperville, Virginia · HMdb – The Gibson House marker · American Battlefield Trust – Upperville. Ride counts from our own Strava and Ride with GPS logs, 2009–2026.
