One of the oldest paved roads in Kentucky, this route was by 1785 the original entry to Bardstown from the east and part of the legendary Wilderness Road. After 1792, Congress ordered the pioneer trace improved as a military road. The cobbled paving on this hill dates to at least circa 1790, allowing two-way traffic by heavy freight wagons and all wheeled vehicles entering and leaving Bardstown. After serving for more than 30 years as the major entry connector to the east end of historic Arch Street, the steep pathway was relegated to light traffic and mounted riders when an improved turnpike was built circa 1830 below the cliffs. Cut off from modern streets after 1925, it survived in isolation and thereafter served only pedestrian traffic. It was placed on the National Registry of Historic Places in 1989.