In the latter half of the 18th through the early 19th century, road building in Virginia was marked by the development of many toll roads, also known as turnpikes. In 1785, when established methods of funding for road improvement and maintenance proved insufficient, gates were constructed along heavy travel and trade routes to collect tolls. These newly established turnpikes got their name from the original toll gate design, which consisted of a turnstile made from two crossed bars, pointed at their outer ends, and turned on a vertical bar. In and around Leesburg, these newly established turnpikes included seven toll gates between Leesburg and Alexandria and four from Leesburg to Georgetown.

The outbreak of the Civil War in 1861 interrupted both general road maintenance and the collection of tolls, and by the early 1870s, the operation of turnpikes in Loudoun and Fairfax County, including Leesburg Turnpike, was abandoned. These routes functioned as standard county roads until 1910 when the Virginia General Assembly authorized the incorporation of the Washington and Leesburg Turnpike Company.