This article explores how school gardens provide learning opportunities for school-aged children while concurrently helping cities achieve sustainability. The authors analyse this process in Washington, DC, a particularly innovative metropolis in the United States. This national capital city boasts two of the most progressive examples of legislation aimed at improving environmental awareness and inciting citizens to engage in environmental stewardship, both of which focus on school-aged children: (1) the "Healthy Schools Act of 2010" and (2) the "Sustainable DC Act of 2012". Together these policies focus on bringing healthy lifestyles and environmental awareness, including meaningful outdoor learning experiences, to students and families in the District of Columbia. This article is organised into three parts. The first part discusses how Washington, DC became a sustainable learning city through the implementation of these specific policies. The next part presents the results of a pilot study conducted in one kindergarten to Grade 5 (K-5) elementary school located in Ward 8, the poorest part of the city. The authors' analysis considers the support and the obstacles teachers and principals in the District of Columbia (DC) are experiencing in their efforts to integrate school gardens into the curriculum and the culture of their schools. Exploring the impacts of the school garden on the students, the local community, and the inter-generational relationships at and beyond schools, the authors aim to shed light on the benefits and the challenges. While Washington, DC is fostering its hope that the benefits prevail as it provides a model for other cities to follow, the authors also candidly present the challenges of implementing these policies. In the final part, they discuss the implications of their findings for school gardens and sustainable learning cities more broadly. They encourage further research to gain more insights into effective ways of promoting environmental literacy and to consolidate the transferability of this model.