Children in Western countries only spend 20 percent of their waking hours in school and there is little attention spent helping children engage in formative experiences in the other 80 percent. Additionally, by 2050 over 70 percent of the world’s children will live in cities. How can developmental scientists, city planners, architects, and educators come together to address this “other 80 percent” of children’s waking hours in places where most children live, for the benefit of children’s development? One answer is the Learning Landscapes initiative, which marries the learning sciences with urban revitalization to craft carefully planned play experiences that focus on learning outcomes, particularly for children and families from under-resourced communities. Playful learning, a broad pedagogical approach featuring child-directed play methods, provides a unique way to foster learning and engagement organically within the built environment. This paper summarizes data from Learning Landscapes projects while reflecting on lessons learned and exploring future directions.