Although numerous research studies have investigated the effects of fatigue in commercial motor vehicle drivers, research with winter maintenance (WM) drivers is sparse. This study pilot-tested the feasibility of evaluating WM operator fatigue during winter emergencies using naturalistic driving data. Four WM operators participated in the study and drove two instrumented snow plows for three consecutive winter months. The operators also wore an actigraph device used to measure sleep quantity. As this was a pilot study, the results were limited and only provided an estimation of what may be found in a large-scale naturalistic driving study with WM operators. Results showed the majority of safety-critical events (SCEs) occurred during the night, and approximately half of the SCEs occurred when participants were between 5 and 8 h into their shifts. Fatigue was identified as the critical reason in 33% of the SCEs, and drivers were found to average less sleep during winter emergencies versus winter non-emergencies. However, one participant accounted for all fatigue-related SCEs. Although data were limited to two instrumented trucks and four drivers, results support the approach of using naturalistic driving data to assess fatigue in WM operators. Future on-road research is needed to understand the relationship between fatigue and crash risk in WM operators.