The Northwestern Virginia Turnpike was started in 1827 to connect Winchester to Parkersburg. It became an important east-west road in what is now West Virginia, later becoming part of U.S. Route 50. This road helped connect the northern part of the state to Baltimore instead of Richmond, which added to the region’s support for the Union during the Civil War.

The road was completed in 1838, before its rival, the Staunton-Parkersburg Turnpike. It was well-organized and funded by the state. Engineer Claudius Crozet planned the route through present-day counties like Hampshire, Preston, and Harrison, and later Charles B. Shaw finished the route to Parkersburg.

The turnpike was successful at first, with toll collections and stagecoach service, but it faced problems like flood damage and railroad competition. After the Civil War, the road fell into poor condition. It wasn't well maintained but eventually became part of the U.S. highway system in the 20th century.