First settled in 1734, it holds two of the oldest standing houses in Loudoun County, "Hunting Hill" and "Foxton Cottage", directly across the Catoctin Creek from each other.
The new settlers called the area Taylor Town, which became Taylorstown around 1900. The Taylorstown Mill was continuously in operation until 1911, when its water wheel was sold to the nearby Oatlands Mill and the mill converted to steam power. In 1932, the steam engines were removed and the Mill became a feed store until Anna Hedrick bought it in the late 1950s. Since the late 1960s, Taylorstown Mill has been a private residence. The private residence today called Whiskey Hill dates to the late 18th century.
During the 19th century, the Taylorstown area was one of the most densely populated areas of Loudoun County. The town had a post office, a blacksmith's shop, 2 mills (one is still standing), a U.S. Government-operated still, general and supply stores and a movie theatre. There are also records of schools, most notably the Crossroads School built in 1834, which was located near Waterford Downs until the 1940s.
Taylorstown is today a community of about four thousand people (3,216 were recorded in the 2000 census, a number that has grown significantly) who live generally within a three-mile radius of the original town center.