Green Pastures (Middleburg, Virginia)

Old Denton is a historic home and farm complex located near The Plains, Fauquier County, Virginia. The property includes a two-story, brick-masonry main dwelling (c. 1860), a secondary dwelling (c. 1820), a meat house (c. 1860), a stable (c. 1936), a tenant house (c. 1950), three early- 20th-century dry-laid stone walls, and an early-20th-century pump. The house features a one-story, negatively sloped, three-bay, classically inspired, Greek Doric order front porch.It was listed on the National Register of Historic Places in 2012.

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).

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.

Burrland Farm Historic District is a historic home and farm complex and national historic district located near Middleburg, Fauquier County, Virginia. The district encompasses 22 contributing buildings, 2 contributing sites, 14 contributing structures, and 1 contributing object on a 458-acre thoroughbred horse breeding and training farm. The buildings were built between 1927 and 1932, and include a Georgian Revival style training barn, a polo barn, a stallion barn, two broodmare barns, a yearling barn, a field shed, an equipment shed, a farm manager's house / office, a trainer's cottage, a mess hall quarters, a foreman's dwelling, three mash houses, five garages, a pumphouse, and a feed and storage warehouse. The contributing structures include a silo, a springhouse, three loading chutes, two teasing chutes, two rings, three run-in sheds, one sun hut and an entrance gate. The original Burrland house was built in 1879 and expanded in 1927 for William Ziegler Jr. by architect William Lawrence Bottomley. Ziegler sold the property in 1955 to Eleonora Sears, who "deliberately gutted and burned [the mansion] down" in 1961. She then sold the farm in 1966.It was listed on the National Register of Historic Places in 1997.

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.

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.

Waverly, also known as Waverley, is a historic house located near Middleburg, Fauquier County, Virginia. The original section was built about 1790, and later enlarged about 1830, and enlarged and remodeled in the 1850s. It is a single-pile, center-hall, two-story dwelling, a typical example of an I-house. It has a long, two-story rear ell and has Gothic Revival style decorative detailing. The front facade features a full-width two-story portico with six square piers supporting a flat roof with a plain wooden parapet. The house was renovated after 1940 by architect David Adler.It was listed on the National Register of Historic Places in 1979.Peyton House, built during 1831–34 in Raymond, Mississippi, appears to have been modeled upon Waverly.

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.

Middleburg Academy ( formerly Notre Dame Academy, a girl's Catholic boarding school, until it went coed in the 1990's, it then became a day school with an enrollment of approximately 150, until it was purchased by Middleburg Academy) Middleburg Academy was a co-educational, nonsectarian, independent secondary school, set on a historic campus of more than 95 acres (38 ha) in Middleburg, Virginia. On June 17, 2020 Middleburg Academy announced its full closure.

The Gen. William Mitchell House, also known as Boxwood or the Gen. Billy Mitchell House was the country estate and home of General Billy Mitchell (1879–1936) during the last ten years of his life, from 1926 through 1936. Mitchell was an American general who is regarded as the father of the U.S. Air Force. He is regarded as one of the most famous and most controversial figures in American airpower history. The house was declared a National Historic Landmark in 1976. It is located about .5 mile south of Middleburg on Virginia Route 626, straddling the county lines of Fauquier and Loudoun Counties. Part of the estate is now home to Boxwood Estate Winery.

Much Haddam is a Federal style brick house, built about 1820 just outside Middleburg, Virginia by Richard Cochran. The two-story brick house is located on the Ashby's Gap Turnpike, near the west end of Middleburg, and is a prominent landmark to those approaching Middleburg from the west.