Heavy snowstorms in Kentucky, while uncommon, often shut down commerce and transportation networks while threatening public safety. An understanding of the teleconnection patterns associated with these storms could benefit many people in the state. In this study, we adapted a snowstorm ranking methodology originally developed for the northeastern United States and applied it to Kentucky. Transportation and population data were used along with snowfall data to rank 26 significant Kentucky snowstorms from 1960–2010. Our results showed that the snowstorm of 6 January 1996 barely edged out the storm of 9 March 1960 to rank as the worst storm in the past 51 winters. Heavy snowstorms in Kentucky tend to be clustered through time and often associated with the warm phase of the Pacific Decadal Oscillation and the negative phases of the North Atlantic Oscillation and Eastern Pacific Oscillation. However, analysis also suggests that several other teleconnection patterns can lead to heavy snowstorms in Kentucky.