Upperville is an unincorporated community in Fauquier County, Virginia, United States, located along U.S. Route 50 fifty miles from downtown Washington, D.C.
Founded in the 1790s along Pantherskin Creek, it was originally named Carrstown by first settler Josephus Carr. Through an 1819 Act passed by the Virginia General Assembly, the name was changed to Upperville. Upperville has been designated as the Upperville Historic District and is a Virginia Historic Landmark that is listed in the National Register of Historic Places. Also listed are Blue Ridge Farm, Oakley, and Rose Hill Farm. Situated eight miles to the west of Middleburg, the Upperville/Middleburg area is home to a number of prominent Thoroughbred horse breeding farms and country estates. Part of Virginia's famous Piedmont horse country, the Upperville Colt & Horse Show was conceived by Colonel Richard Henry Dulany and first held in 1853. It remains the oldest such event in America. A Dulany family member owned Oakley Farm. It was the site of two battles during the American Civil War. Near Upperville, Californian Henry T. Oxnard built a horse breedingoperation in 1903 that he named Blue Ridge Farm. Purchased by Rear Admiral Cary Travers Grayson in 1928, members of the Grayson family still own the property which too is listed in the National Register of Historic Places.