The Kentucky Transportation Cabinet (KYTC) and Kentucky Transportation Center (KTC) at the University of Kentucky developed and performed an assessment of the vulnerability of the state’s national highway system (NHS) to extreme weather events and natural hazards. The assessment was designed as a hybrid process that 1) gathered and analyzed existing and available quantitative data on natural hazards, including meteorological hazards and geological hazards; 2) executed a series of workshops at KYTC districts throughout the state to elicit local expert knowledge on transportation system vulnerabilities; and 3) incorporated all data into a single vulnerability assessment. The workshops involved several facilitated exercises, including map-based discussions and keypad exercises to identify vulnerabilities along highway segments. Data from the mapping and keypad exercises were gathered in a geographic information system (GIS) and combined with the other hazard data to identify vulnerabilities for each highway segment. FHWA’s Vulnerability Assessment Scoring Tool (VAST) was used to process all the data into a single and ultimate assessment. Results from this analysis include a district-level prioritized ranking of NHS segments based on their vulnerability to extreme weather and natural hazard events. Additionally, a district vulnerability assessment report for each district highlighted the most vulnerable assets in the district and discussed their vulnerabilities in detail. This research is intended to aid KYTC in identifying at-risk infrastructure and direct the implementation of preparedness and resilience measures, thus helping to protect the integrity of the transportation system and the sound investment of taxpayer dollars.