- Background To decide whether to cross the road, one is first required to judge whether the crossing place is safe. Young children have impoverished crossing skills manifested in lower awareness toward potential hazards, situation awareness and overall readiness for crossing. The aim of this study was to identify the environmental features that make children think a place is safe or dangerous for crossing. Methods 24 children in three age categories (ages 7–8, 9–10, 11–13) and 12 adults viewed 41 still images of real-world road-side scenes on a wide screen, and were asked to rate each scene for safety of crossing as fast as possible using a slide bar (0–100). Safety evaluation and the time to decision were recorded. Each scenario was classified by the elements of the environment: the urban area it was located in (e.g., commercial, residential), crossing location, proximity to road features (e.g., junction), road type, number of lanes, and distractors in the environment. Results Children in all age categories estimated crossing safety mainly by obvious conspicuous features, like presence of a crosswalk, which anchored their decision. They were indifferent to certain relevant factors (e.g., number of lanes). In contrary, adults seemed to base their decision more on higher order reasoning (e.g. the duration of exposure to danger derived from the number of lanes). In general, children felt less secure when coming to cross the road, and it took them longer to reach a decision on the crossing location’s safety level. When the decision was made, answers were more diverse than for adults. Conclusions Children and adults use different strategies to estimate the safety level of a certain place for crossing. It seems that adults relay more upon sophisticated decision making processes that improves with age and experience. In contrary, children, even as old as 13 years-old, often rely on the fact that a place is designed for crossing as a guaranty for their safety.