Middleburg Academy

Saint Louis is an unincorporated community in southwestern Loudoun County, Virginia. Saint Louis is located near the intersection of Saint Louis Road (Virginia State Route 611) and Snake Hill Road (Virginia State Route 744), six miles west of Middleburg. It is a historic African American community dating from 1891 or earlier, with many African Americans still living there today. Banneker Elementary School is located in Saint Louis.

Mill House, also known as Chinn's Mill and Hatcher's Mill, is a historic grist mill complex located near Middleburg, Fauquier County, Virginia. All of the buildings in the complex are constructed of stone laid in a random-rubble pattern and some are of mixed stone and frame construction. They represent a late 18th- to early 19th-century rural Virginia grist mill operation, that was later transformed during the early-20th-century into a "hunt country" estate by John Shaffer Phipps. In addition to the mill itself, the complex includes the miller's house, the cooper's house and shop, the mill owner's house, and what was likely a dairy/smokehouse.It was listed on the National Register of Historic Places in 1984.

Benton, also known as Spring Hill, is a house in Loudoun County, Virginia, near Middleburg. The house was built by William Benton, a brickmaker and builder, around 1831. Benton had made a journey to Wales to collect an inheritance shortly after 1822 and there saw a house that he admired and wished to replicate on his own lands. He called the house "Spring Hill."

Wexford, also known as Kennedy Retreat at Rattlesnake Ridge, is a 167-acre (0.67 km2) ranch amid the Blue Ridge Mountains in unincorporated Marshall, Virginia, located 4 miles (6 km) northwest from Middleburg (about 50 miles (80 km) from Washington, D.C.). The property was acquired, designed, and named by Jacqueline Kennedy in 1962 as a weekend retreat during John F. Kennedy's presidency. Its namesake is the ancestral home of the Kennedy family. Following their visit to Wexford (Ireland) in June 1963, Éamon de Valera gifted 3-year old John F. Kennedy Jr. a pony, which was stabled at Wexford (ranch). It is the only home John and Jacqueline built together during their marriage, and was the last place they vacationed before his assassination in November 1963. John Jr. practiced his father's iconic final salute at Wexford.Ronald Reagan leased Wexford from William Clements for his residence and headquarters during the 1980 Presidential Campaign. It is the only private retreat used by more than one President of the United States (many presidents have used the state-owned Camp David).

Atoka Historic District is a national historic district located at Atoka, Fauquier County, Virginia. It encompasses 11 contributing buildings in the rural crossroads of Atoka. They include four dwellings and their various outbuildings, two commercial buildings, and a stone spring house. Notable buildings include the Caleb Rector House (c. 1830), the Atoka Store (c. 1893), and the Rector-Deane House (1893).It was listed on the National Register of Historic Places in 2004. It is included in the Cromwell's Run Rural Historic District.

Atoka is an unincorporated hamlet in Fauquier County, Virginia, United States. Atoka is located along U.S. Route 50 4 miles (6.4 km) west of Middleburg. The Atoka Historic District, which is listed on the National Register of Historic Places, is located in Atoka. The Goose Creek Stone Bridge is located near Atoka in Loudoun County, Virginia.

Welbourne is the main house of what was formerly a large plantation in Loudoun County, Virginia. The original core of the house, in what is now the south wing, was built about 1770. The stone house was two and a half stories tall, with three bays, one room deep. Some of the original woodwork survives in this section of the house. The house was expanded greatly by John Peyton Dulany around 1830, adding five bays in stuccoed brick, connected to the original house by a transverse hall. The interior of the new section features Greek Revival detailing. A two-story portico with Italianate columns was added in the 1850s, and the house was further enlarged with a two-story addition on the south side in the 1870s. The whole is covered with stucco, detailed with faux-painted joints.The house faces an axial lane through a park-like setting. The house's surroundings include a designed garden to the east with one of the oldest swimming pools in Virginia. The property includes a number of outbuildings, including a tenant house, spring house, servants' house, toolhouse, smokehouse and a schoolhouse, as well as a subsidiary dwelling reputed to be older than the main house.The house has remained in the hands of Dulany descendants. It was listed on the National Register of Historic Places on February 23, 1972, and is operated as a bed-and-breakfast inn.

Crednal is a historic home located near Unison, Loudoun County, Virginia, United States. The building is an example of an early-19th-century, Federal-style, two-story, five-bay, brick dwelling built in 1814, that was constructed around an existing 18th-century, vernacular, residential stone core. A two-story, three-bay frame wing was constructed in 1870. In 1993, a two-story, two-bay, Greek Revival-style brick dwelling that had been slated for demolition from Greene County, Virginia, was moved to the property and attached to the house by a hyphen. Also on the property are the contributing Carter family cemetery and an unmarked slave cemetery.It was listed on the National Register of Historic Places in 2011.

Huntland, originally known as New Lisbon, is a historic estate located at Middleburg, Loudoun County, Virginia. The original section was built in 1834, and is a two-story, five bay, Federal style brick dwelling. It built by master brickmason William Benton Sr., who also constructed nearby Oak Hill, the home of President James Monroe. In 1915, the house was remodeled and enlarged with side one-story brick additions and Colonial Revival-style detailing. The estate was also enhanced with gates, walls, and terraced gardens that are reminiscent of English manor estates and state-of-the-art kennels and horse stables. Also on the property are the contributing spring house, smokehouse, and a guest cottage, all constructed around 1834, and early-20th-century structures that include secondary dwellings, a dairy barn with attached silos and a corncrib, a milking parlor, five sheds, a garage, a pump house, and a cistern.The Huntland estate was once devoted primarily to foxhunting, a sport that reinvigorated the economy of the region in the early-20th century. Between 1955 and 1963, the estate was owned by George R. Brown and Herman Brown of Houston, Texas, and Huntland became a retreat for notable Washington dignitaries including Lyndon B. Johnson. In 1962, secret international negotiations were conducted at Huntland that resulted in the New York Agreement between Indonesia, the Netherlands and the United Nations centering on the future of Western New Guinea.It was listed on the National Register of Historic Places in 2013.

The Battle of Middleburg took place from June 17 to June 19, 1863, in Loudoun County, Virginia, as part of the Gettysburg Campaign of the American Civil War. Confederate Maj. Gen. J.E.B. Stuart, screening Robert E. Lee's invasion route, sparred with Maj. Gen. Alfred Pleasonton's Union cavalry. On June 17, Col. Alfred N. Duffié's isolated 1st Rhode Island Cavalry Regiment was attacked by the brigades of Thomas T. Munford and Beverly Robertson. The 1st Rhode Island was routed, taking about 250 casualties. On June 19, J. Irvin Gregg's brigade advanced, driving Stuart's cavalry one mile beyond the town. Both sides were reinforced, and mounted and dismounted skirmishing continued. Stuart was gradually levered out of his position but fell back to a second ridge, still covering the approaches to the Blue Ridge gap.

The Goose Creek Stone Bridge crosses Goose Creek in Loudoun County, Virginia. The 200-foot (61 m) long stone arch bridge spans the creek in four arches. Built about 1810, it is the largest stone turnpike bridge in northern Virginia, designed to carry the Ashby's Gap Turnpike across the creek. The turnpike was replaced by U.S. Route 50, which crosses the creek a short distance to the south. The bridge is no longer used for vehicular traffic. The bridge was a center of fighting in the American Civil War on June 21, 1863, during the Battle of Upperville. The Goose Creek Bridge was placed on the National Register of Historic Places on October 9, 1974.

Leithtown is an unincorporated village in Loudoun County, Virginia. Leithtown lies to the west of Goose Creek at the crossroads of Foxcroft, Pot House, and Mountville roads. It is the home of the Foxcroft School and saw cavalry action in the Battle of Middleburg and Battle of Upperville in 1863.