Communities around the world lack safe places for children to play and be physically active. One solution to this issue is Play Streets, which involves the temporary closure of streets for several hours to create a safe space for active play and physical activity. While the benefits of these programs are greater when they are recurring over many years, there is a dearth of literature regarding how to successfully sustain Play Streets. To understand how Play Streets can be sustained in the long term, we conducted semi-structured interviews with 24 Play Streets organizers representing 22 Play Streets programs across the United States. Four recurring sustainability challenges were highlighted from the thematic analysis: 1) securing and sustaining funding, 2) managing community and city resistance to street closures, 3) navigating government bureaucracy, and 4) retaining interest amongst organizers and volunteers. With each challenge, we describe how Play Streets organizers navigated those challenges, with a goal of generating recommendations for those wishing to sustain Play Streets programs in the long term.