This study aims to examine child pedestrian safety around parks by considering four rule-compliance measures: temporal, spatial, velocity and visual search compliance. In this regard, street crossing observations of 731 children were recorded at 17 crosswalks around four parks in Montreal, Canada. Information on child behaviors, road features, and pedestrian–vehicle interactions were gathered in three separate forms. Chi-square tests were used to highlight the individual, situational, behavioral and road environmental characteristics that are associated with pedestrian rule compliance. About half of our sampled children started crossing at the same time as the adults who accompanied them, but more rule violations were observed when the adult initiated the crossing. The child’s gender did not have a significant impact on rule compliance. Several variables were positively associated with rule compliance: stopping at the curb before crossing, close parental supervision, and pedestrian countdown signals. Pedestrian–car interaction had a mixed impact on rule compliance. Overall, rule compliance among children was high for each of our indicators, but about two-thirds failed to comply with all four indicators. A few measures, such as longer crossing signals and pedestrian countdown displays at traffic lights, may help to increase rule compliance and, ultimately, provide safer access to parks.