In recently, a growing concern for the health of urban residents increased interests in a variety of outdoor activities simply be done in terms of cost and time. They are specially interested in low-impact and safe exercises around residential or working area. Walking is the one of easily doing exercise in daytime or nighttime near residential area. The sidewalks of boulevard near the residential area is the best place for exercise because of easy access and the green space with roadside trees. However, if the nighttime is not guaranteed the proper lighting condition, the possibility of exposure to crime and the threat to pedestrian safety can be increased. Because roadside trees are one of the potential obstacle for lighting condition, supplementary lightings are important to mitigate interruption for safety. To meet such a need, the purpose of this study is to propose a simulation approach which improves lighting condition on sidewalks of boulevard with variety of roadside trees. To do so, the simulation approach is applied for analyzing the interrupted condition by classified five standard types of roadside trees considering the growth of them and finding optimal layout of supplementary luminaires by lighting types. The results of this approach shows that it is useful for assessing the safety of pedestrian in nighttime.