The purposes of this study were to examine perceptions of places to play and be physically active among children from two different urban neighborhoods, and evaluate these perceptions for age-related developmental differences. One hundred and sixty-eight children from grades K-6 (aged 6–12 years old) completed mental maps depicting places where they could play and be physically active. The children were recruited from schools in two neighborhoods—one a high-walkability (H-W) grid-style neighborhood, the other a low-walkability (L-W) lollipop-style (i.e., cul-de-sacs) neighborhood. Analysis revealed that children in the H-W neighborhood depicted more active transportation and less non-active transportation than children in the L-W neighborhood. Children in the lowest grades (K-2) in the L-W neighborhood depicted more play in the home/yard environment than the oldest children, more good weather image events than children in Grades 3–6, and less play outside the home/yard environment than children in Grades 3 and 4. In the H-W neighborhood, the youngest children (K-2) depicted significantly less play in the home/yard environment and less play outside the home/yard environment than older children (Grades 3–6). Thus, both the type of urban neighborhood and children’s age moderated perceptions of places to play and be physically active.