Children from under-resourced communities regularly enter formal schooling lagging behind their peers. These deficits in areas such as language development, reading readiness, and even in the kind of spatial skills that predict later mathematical knowledge, may persist throughout their lifespan. To address such gaps, policymakers have focused largely on schooling as the great equalizer. Yet, children only spend 20% of their waking hours in school. How can developmental scientists and educators address this "other 80%" for the benefit of children's development? One answer is the Learning Landscapes initiative, which involves crafting 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. Learning Landscapes already incorporates several well-documented projects. The Ultimate Block Party brought over 50,000 people to Central Park to engage in playful learning activities. Supermarkets became hotspots for caregiver-child interaction by simply adding prompts for caregiver-child interaction through signage in everyday "trapped" experiences. Urban Thinkscape transformed a bus stop and adjacent lot into a hub for playful learning while families were waiting for public transportation. Finally, Parkopolis is a life-size human board game that fosters STEM and reasoning skills in public spaces. This paper reflects on data from these projects while reflecting on lessons learned and future directions.