Rutledge Farm

The Oakham Farm is a historic farm at 23226 Oakham Farm Lane, near Middleburg in Loudoun County, Virginia. The farm includes 100 acres (40 ha) of land north of United States Route 50, with its building complex anchored by a farmhouse built in 1847 and repeatedly altered. The main portion of the farmhouse is a 1920s three-story Classical Revival block, which has the original 1847 two-story Greek Revival house attached as an ell to one side, along with another c. 1840 structure that may have functioned as a separate kitchen. The property was first developed by the Peyton family, with its present buildings dating to the ownership of the Rogers family. During the American Civil War, Oakham was where the irregular Confederate Army unit known as Mosby's Rangers was organized.The farm was listed on the National Register of Historic Places in 2016.

The Little River Rural Historic District encompasses a large rural landscape in northeastern Fauquier County. Covering some 23,000 acres (9,300 ha), the district extends from near The Plains in the south to near Middleburg in the north. On the east it is bounded by the Bull Run Mountains, and on the west by Cromwell's Run. The area's landscape typifies the characteristics of the Piedmont region of Virginia, and is devoid of high-density residential, commercial, or industrial activity. Land use is largely devoted to agricultural, equestrian, and hunting pursuits. There are a few places where mills historically operated, and there are three small village centers in the district. A portion of the Middleburg battlefield lies in the northern part of the district, and the district encompasses several previously listed areas, including the Burrland Farm Historic District, the Gen. William Mitchell House (a National Historic Landmark), the Waverly house, Old Denton, and Green Pastures.The district was listed on the National Register of Historic Places in 2014.

Dover is an unincorporated community in Loudoun County, Virginia, United States. Dover is located east of Middleburg at the intersection of U.S. Route 50, Champe Ford Road (SR 629 south), and Cobb House Road (SR 629 north). The Little River begins following Route 50 at this point. Dover as a geographical entity is somewhat exaggerated, seeing as the bend in Route 50 it refers to consists of only few houses, but it has a long pedigree as a named area, appearing on state and national maps. Most likely, its status as a geographical entity stems from the fact that the Little River Turnpike (first toll road in America) and Aldie-Ashby's Gap Turnpike terminated approximately together here, 1.3 miles west of Aldie.

Furr Farm is a historic home and farm located at Aldie, Loudoun County, Virginia. The house is a two-story, five bay, frame structure with a side gable roof and exterior end chimneys. The property includes two contributing frame barns.It was listed on the National Register of Historic Places in 2012.

Stoke is a historic farm property at 23587 Stoke Farm Lane in rural Loudoun County, Virginia, near the hamlet of Aldie. Its main house, set one mile down the entrance drive, is an 1840 Greek Revival farmhouse that underwent a major transformation in 1907 in the Renaissance Revival style. The property includes an early 20th-century swimming pool, tennis court, and landscaped garden with wall fountain, in addition to a complex of farm outbuildings, many dating to the 1920s. The gardens were developed by noted horticulturalist Eleanor Truax Harris.The property was listed on the National Register of Historic Places in 2015.

The Battle of Aldie took place on June 17, 1863, in Loudoun County, Virginia, as part of the Gettysburg Campaign of the American Civil War. Maj. Gen. J.E.B. Stuart's cavalry screened Gen. Robert E. Lee's Confederate infantry as it marched north in the Shenandoah Valley behind the sheltering Blue Ridge Mountains. The pursuing Union cavalry of Brig. Gen. Judson Kilpatrick's brigade, in the advance of Brig. Gen. David McMurtrie Gregg's division, encountered Col. Thomas T. Munford's troopers near the village of Aldie, resulting in four hours of stubborn fighting. Both sides made mounted assaults by regiments and squadrons. Kilpatrick was reinforced in the afternoon, and Munford finally withdrew toward Middleburg.

Institute Farm, also known as the Loudoun Agricultural and Mechanical Institute, was the first agricultural school in Virginia and one of the earliest institutions devoted to agronomy in the United States. Located near Aldie, Virginia, the school was established as the Loudoun County Agricultural Institute and Chemical Academy around 1854 on a former portion of U.S. President James Monroe's Oak Hill plantation.

The Red Fox Inn & Tavern, also known as the Middleburg Inn and Beveridge House, is a historic inn and tavern located in Middleburg, Loudoun County, Virginia. According to the National Register of Historic Places placard on the building, the Red Fox Inn was established circa 1728. Some historic artifacts on the building date to about 1830, with additions and remodelings dating from the 1850s, 1890s, and the 1940s. It consists of a 2 1/2 story-with-basement, five-bay, gable-roofed, fieldstone main block, with a two-story, three-bay, gable-roofed fieldstone rear wing. The front facade features a one-story, one-bay, pedimented porch dating from the 1940s. It has a standing seam metal gable roof and exterior end chimneys. The buildings exhibits design details in the Federal and Colonial Revival styles. It is thought to be one of the oldest continuously operated inns in Virginia as well as the United States. The Red Fox Inn & Tavern has served a variety of functions including: stagecoach stop, inn, tavern, butcher shop, apartment house, post office, and hotel.It was listed on the National Register of Historic Places in 1997.

Mountville is an unincorporated community in the Loudoun Valley of Loudoun County, Virginia. The village is situated on Snickersville Turnpike halfway between Aldie and Philomont at the intersection of Mountville Road. Mountville is located on a promontory between the main branch of the Goose Creek and its tributary, Beaverdam Creek, at the western base of Catoctin Mountain. Despite its geographic location, Mountville is named, not for its elevation, but rather for Ezekial Mount, who first settled the area in 1797, after moving to Loudoun from Mountville, Pennsylvania. The village was officially christened Mountville in 1817 with the establishment of a post office in the village bearing that name. Mountville was the scene of early skirmishing during the American Civil War Battle of Unison

The Middleburg Virginia AVA is an American Viticultural Area in the northern Piedmont region of Virginia, 50 miles (80 km) west of Washington, D.C. It is named for the town of Middleburg, Virginia and is bounded by the Potomac River to the north and by mountains in other directions. The hardiness zone of the AVA is 7a.

The Middleburg Historic District comprises the historic center of Middleburg, Virginia. The district extends along the downtown section of Washington Street, and is flanked on the east by Independence Street and to the west by Constitution Street. The district's commercial area is along Washington and Madison Streets. Middleburg was established in 1787, but the historic district includes a few 18th-century structures, with most dating to the mid-19th century. The district includes the Red Fox Inn & Tavern, the oldest building in town and listed individually on the National Register of Historic Places. Most of the structures in the core of the district are Federal style townhouses.The most notable house in the district is "Chestnut Hill", also known as "The Hill," a large Federal-style house sitting apart surrounded by lawns. The district also features four churches. Little development took place in Middleburg in the late 19th century, and the district includes no examples of Victorian architecture. The district does include a few early 20th-century commercial structures.The Middleburg Historic District was placed on the National Register of Historic Places on October 29, 1982.

The Hill School is a private, K-8 co-educational day school in Middleburg, Virginia, United States that was established in 1926.