Weather conditions are significant hazards impacting the safe and efficient operation of aircraft. In this study, a large number of pilots were surveyed regarding weather events, and the circumstances associated with those events. Pilots completed a web-based questionnaire containing demographic questions, a risk perception scale, a hazardous events scale, and a pilot judgment scale. The pilots who reported a flight in which they penetrated weather without authorization or were concerned about the weather also completed 53 questions regarding their weather encounter. Usable data were obtained for 364 participants: 144 who reported flying into weather, 114 who experienced a flight on which weather was a concern, and 106 who reported no flights on which weather was entered or was a major concern. Significant differences were evident between the three groups on the measures of pilot judgment, personal minimums, and hazardous events where pilots flying into weather recorded the poorest scores (least conservative minimums, most hazardous events, and poorest judgment). Significant differences were also noted between the two weather groups for a number of circumstances surrounding the events. Compared to the in-weather group, pilots in the near-weather group had acquired greater instrument hours, were older, and were more likely to have an instrument rating. Their aircraft were more likely to have an autopilot. More pilots in the in-weather group (28%) reported that they would be much more careful in the future regarding weather, compared to 17% of the near-weather group. The study provides data not previously obtained on both the situational and personal characteristics that are related to involvement in different degrees of weather-related encounters. These data should promote a better understanding of these individuals and the situations in which they are involved, and should inform future research and intervention efforts.