Covering approximately 16,200 acres in western Albemarle County and a small corner of Nelson and southeastern Augusta counties, the Greenwood-Afton Rural Historic District was first settled by Europeans with the arrival of 18th-century Scots-Irish immigrants from the Shenandoah Valley. Early settlement developed along wagon roads and turnpikes that passed through gaps in the Blue Ridge Mountains. During the second-quarter of the 19th century, French-born military engineer Claudius Crozet, known as the “Pathfinder of the Blue Ridge,” directed the building of four railroad tunnels through the mountains, including one that was the longest in the U. S. when it opened in 1858 (reopened in 2021 as a hiking trail). The advent of rail transport dramatically boosted agriculture and trade in the Greenwood-Afton district, giving rise to one of Virginia’s most successful early commercial orchard industries. Today the Greenwood-Afton Rural Historic District is dominated by large farmsteads, the Blue Ridge Parkway, and early-20th-century estates. It also includes the mid-19th-century villages of Greenwood Depot and Afton, as well as the early-20th-century historically African American communities of New Town and Free Town. Greenwood’s legacy as a seasonal playground for the wealthy is reflected in the area’s large number of estates and “country houses” designed by prominent architects.

In early 2016, a small boundary increase to the original Greenwood-Afton Rural Historic District was approved for inclusion in the National Register, adding several properties along Howardsville Turnpike adjacent to the Swannanoa property.
[NRHP Approved: 2/8/2016]