We investigated the effects of pedestrian environments on parents’ walking behavior, their perception of pedestrian safety, and their willingness to let their children walk to school. This study was a simulated walking environment experiment that created six different pedestrian conditions using sidewalks, landscape buffers, and street trees. We used within subjects design where participants were exposed to all six simulated conditions. Participants were 26 parents with elementary school children. Sidewalks, buffer strips, and street trees affected parents’ decisions to: walk themselves; let their children walk to school; evaluate their perception whether the simulated environment was safe for walking. We found that the design of pedestrian environments does affect people’s perceptions of pedestrian safety and their willingness to walk. The presence of a sidewalk, buffer strip, and street trees affected parents’ decision to walk, their willingness to let their children walk to school and perceived the pedestrian environment as safer for walking. The effects of trees on parents’ walking and perception of pedestrian safety are greater when there is a wide buffer rather than a narrow buffer. It was found that parents are more cautious about their children’s walking environments and safety than their own.