Using a virtual road crossing environment, the reported research investigated the road crossing behavior of 12 male pedestrians in familiar and unfamiliar environments. Environment familiarity was manipulated using traffic direction. Seven of the participants were from a country where traffic flows from right to left and five were from countries were traffic flows from left to right. Each participant was asked to cross the road when traffic was coming from both the familiar and the unfamiliar direction for them. Results showed that pedestrians had lower safety ration, or a lower margin of error, in crossing the road when traffic was flowing in an unfamiliar direction, suggesting that pedestrians might be at greater risk of accident in such environments. Implications of these findings are discussed.