Upperville Historic District

Upperville is an unincorporated village in Fauquier County, Virginia, United States, along U.S. Route 50 fifty miles from downtown Washington, D.C., near the Loudoun County line. 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. John Updike wrote of Upperville in his sardonic 1961 poem Upon Learning That a Town Exists Called Upperville.

Upperville United Methodist Church is a historic church in Upperville, Virginia, United States, on Delaplane Grade Road, just off U.S. Route 50. The single-room church is a brick structure built in 1833, with 15-foot-high windows on its side. During the Civil War, it was used as a hospital, as were many other local churches. Originally, the church had a slave balcony wrapping around its whole length, but the balcony was destroyed during the war to use for firewood, and was later partially rebuilt. The cornerstone near the top of the building reads "METHODIST E. CHURCH. DEDICATED NOVEMBER 3, 1833." The church is part of the Upperville Historic District, which was added to the National Register of Historic Places in 1972.

Green Garden is a historic home and farm located near Upperville, Loudoun County, Virginia. The house was built in four phases. The original section of the house was built about 1833, and is a portion of the rear ell. The main block was built about 1846, and is a two-story, five-bay, single pile brick structure in the Greek Revival style. A two-story rear ell was added about 1856, and it was connected to original 1833 section with an extension in 1921. The front facade features a three-bay porch with full Doric order entablature. Also on the property are the contributing root cellar (c. 1833), a smokehouse (c. 1847), a barn (c. 1870), a garage/office building (c. 1950), and ice house.It was listed on the National Register of Historic Places in 2007.

Oakley is a historic home and farm located near Upperville, Fauquier County, Virginia.

Blue Ridge Farm is a historic home and farm located near Upperville, Fauquier County, Virginia.

Llangollen Farm is an historic American horse and cattle farm located in western Loudoun County, Virginia on Trappe Rd. near Upperville at the foot of the Blue Ridge Mountains. Eight miles (13 km) from the town of Middleburg, the area is home to a number of prominent Thoroughbred-breeding farms and a large country estates. The farm was listed on the National Register of Historic Places in 2017.

The Battle of Upperville took place in Loudoun County, Virginia on June 21, 1863 during the Gettysburg Campaign of the American Civil War.

Willisville is an unincorporated community in southwestern Loudoun County, Virginia, about sixteen miles from the county seat, Leesburg. Willisville is located at the crossroads of Willisville, Millville, and Welbourne Roads. It is named after freed slave Heuson Willis, who bought a cabin and three acres of land shortly after the American Civil War. The tight-knit predominantly African American community of about a dozen houses and church became one of the last communities in wealthy Loudoun County without running water.The Virginia Piedmont Heritage Area Association campaigned to have Willisville designated an historic site. Historic Preservationist Jane Covington finalized the nomination application for the historic village to be listed in the National Register of Historic Places, and has submitted it to the Virginia Department of Historic Resources (VDHR) for review at their September 2019 quarterly meeting. Willisville was added to the National Register in 2019.

Newstead Farm is a Thoroughbred horse breeding farm near Upperville, Virginia founded in 1936 by Taylor Hardin. Following Hardin's death in 1976, the farm was operated by a trust that included his son, Mark. The property was eventually sold to Bertram and Diana Firestone.In July 2018 the Firestone family placed the estate on 353 acres up for sale with a price of $13,500,000 Per Bertram "... time marches on and we have slowed down our various pursuits. We feel it is time to turn the reins over to a new owner that will be able to use and enjoy the farm to its fullest capacity." The farm sold for $9.5 million in March 2020.

Paris Mountain is a peak of Blue Ridge Mountain on the border of Loudoun County and Clarke County in Virginia. The 1,926 feet (587 m) peak, which is located just north of Ashby's Gap and the town of Paris, for which it is named, represents the highest elevation in both counties. The peak is accessible by Blue Ridge Mountain Road from the gap. The Appalachian Trail crosses the western slope of the peak.

Howardsville is an unincorporated community in southwestern Loudoun County, Virginia. It is located at 39°2′16″N 77°50′19″W.