Literally the middle burg (town) on the turnpike between Alexandria and Winchester (though closer to the latter city), Middleburg was probably settled c. 1731. It was laid out on a small grid plan in 1787 by Leven Powell as a coach stop on the turnpike and is still dominated by that route, now U.S. 50, or Washington Street. It prospered and became one of the largest towns in the Northern Piedmont and the center of fierce Confederate loyalty during the Civil War. It declined after the war until the 1900s, when it became the center for the horse and country house set of the area. Today it is the main shopping center for the hunt country, and consequently Washington and its major cross street, Madison, have received an extensive boutique treatment. The town contains an impressive number of early buildings that cluster along Washington Street.
The Red Fox Inn ( NP16.1) (c. 1750, c. 1790, many later alterations; 2 East Washington Street), also known by other names, may contain the remains of the early coach inn, but the large three-and-one-half-story stone structure one sees from the street dates from c. 1790. A large two-story porch originally dominated its front. The most interesting exterior feature is the tall single chimney on the east end (as compared to twin chimneys on the west wall). Across Madison Street is the Noble Beverage house (1824; 2 West Washington Street), a thoughtfully designed structure in which, although it is of brick, the builder matched the scale of the Red Fox Inn and duplicated the twin end chimneys. Farther west on Washington, at the southeast corner of Pendelton Street, is the United Methodist Church (1858, later interior remodeling), a robust Italianate structure with very large exterior brackets. Farther west, on the south side of Washington Street with an entrance from Plains Road, is Vine Hill, or the National Sporting Library and Chronicle of the Horse (1804, later enlargements; 1998, restoration and conversion, Earth Design Associates), a large brick house in the Federal style with three irregular bays in the main structure. Across Washington Street is the Middleburg Community Center (1948, William Bland Dew), a big Colonial Revival building that cries out for some energy in its design. Back east on Washington Street at the center of town is the former Middleburg National Bank Building (1937, Will Hall; 1 East Washington Street, southeast corner of Washington at Madison streets), an unusual design that employs fieldstone for the structure, though the details are the usual banker's dress of classical ornament, in this case including a heavy Doric portico. Farther east is Emmanuel Episcopal Church (1842, altered 1927 and later; 105 East Washington Street), which, with its plain brick front and Gothic arches, recalls Maximilian Godefroy's St. Mary's Chapel (1806–1808) in Baltimore and may indicate the origin of its unknown architect. The awkward stepped cornice from which the finials have obviously been removed is replayed in several Virginia churches. Two bays were added to create the chancel.