Despite the beneficial effects of physical activity (PA), only 26% of children in Germany meet the WHO’s recommendations. Because active play contributes to PA and is accepted by families, the creation of “playable” environments could promote PA. This study is a natural experiment that was conducted to investigate whether slight changes in the physical environment can increase PA in children. In autumn 2016, 140 students from two primary schools located in a deprived district of Leipzig (Germany) gathered ideas on PA-promoting street designs. After protracted negotiations with the city administration, two footpaths were decorated with colored markings (hopscotch grids, labyrinths, “mirror me”) in September 2019. 48 observations were made before (August 2019) and after (September/October 2019) the implementation using the System for Observing Play and Recreation in Communities (SOPARC). Age, gender, activity level, bike use, and interactions with the colored markings were recorded. A total of 5455 individuals (including 1099 cyclists) were observed. Almost one fifth of the observed children (0 to 12 years) interacted with the markings. There was a slight increase in vigorous activity in all observed individuals after the implementation (2.9% vs. 6.4%, p < 0.001). The chance for vigorous activity was higher on decorated footpaths (OR 2.45, CI 1.54–3.89, p < 0.001), for children (OR 19.32, CI 13.07–28.56, p < 0.001), and on Sundays (OR 3.39, CI 2.33–4.94, p < 0.001). The participatory development and design of footpaths that support spontaneous active play “on the way” might be one component that can be used to support changes in children’s PA behaviors and social interactions.