This paper evaluates the traffic safety along freight intermodal connectors (FICs), which are also known as “first mile/last mile roadways,” connecting facilities that link freight-intensive land uses to main freight routes. Using Tennessee’s FICs as a case study, the paper digests the safety with reference to crash frequency, crash rates, and statistical significance of attributing traffic and geometric factors. It was found that connectors leading to pipeline terminals have high crash rates (almost double) compared with other type of terminals, whereas port terminal connectors have the lowest safety problem indices. The study established correlative contributing causes of crash frequencies and rates along FICs that included average annual daily traffic, lanes, shoulders, access, and median types. Traffic signal density was found to strongly and significantly affect the probability of crashes, together with the presence of a two-way left-turn lane (TWLTL), which surprisingly tends to decrease the probability of crashes along these connectors. The presence of shoulders along intermodal connectors was found to help reduce the probability of crashes, whereas the presence of curb and gutter tends to increase crash frequency. Analysis indicated that most of the FICs with high crash rates were also operating at a lower traffic operations level of service (LOS), especially for critical movements toward freight facilities because of high truck volumes.