Mount Sterling, the seat of Montgomery county, was settled in the late 1700s and was originally known as Little Mountain Town. It was renamed Mount Sterling in 1792 for Stirling, Scotland, the home of one of the town founders. The Montgomery Court House post office opened in 1801 and was renamed in 1807. The population in 1990 was 5,362.

Mount Sterling was the western terminus of the Mount Sterling-Pound Gap road, the longest pre-Civil War state road. It was surveyed beginning in 1817 and extended to beyond Prestonsburg, a total of ninety four miles. It became the major overland route to Virginia and the east. Maintenance was a continuing problem and it was turned over to the counties in 1838 and fell into disrepair. The present highway US 460 follows the approximate route of the original road.

The Montgomery county courthouse in Mount Sterling.