Learning and development occur over time across multiple settings both in‐ and out‐of‐school. However, educational programs have not been designed for coordination across settings. Successfully supporting community‐wide youth learning requires greater understanding of how youth may move between settings and the learning pathways available to them. We investigated this topic with data from the adult leaders of 17 programs that participated in a regional summer learning initiative. Respondents tended to conceptualize within‐program pathways (e.g., offering more advanced activities in their organization to current participants) but rarely described actively encouraging youth to move to related programs in other organizations. The results suggest that realization of supportive communities for cross‐program learning and development will require shifts in models of knowledge sharing and program incentive structures.