Railway-caused bear mortality is a concern in the Canadian Mountain National Parks. This research examined the behavioral responses of bears and oncoming trains to better understand what bears perceive as ‘risky’ in bear-train encounters. I used videos of bear-train interactions to measure site-specific variables at bear-train encounter sites to explain a bear’s flight initiation distance (FID) and Flee Speed from an oncoming train. I found that a bear’s FID to an oncoming train was best explained by an interaction between Train Speed and Slope, and between Longitudinal Visibility and Perpendicular Visibility, and that their Flee Speed was best explained additively by Species (bear), Train Speed, the bear’s distance from the track and the between-side difference in Delta Density of Overhead Vegetation. These results can be used to help make site-specific mitigations to areas of the railway where a bear might deem the location more ‘risky’.