There is solid consensus among researchers, program providers, and families that participation in constructive activities during out-of-school time hours can contribute to a youth's healthy and positive development. This paper explores some of the key issues and challenges facing program and city leaders in creating and sustaining afterschool program opportunities that engage the interest and participation of high school age youth. The authors discuss effective program characteristics and strategies for citywide collaboration, along with steps for cities and organizations to build their capacity to meet the needs of today's teen youth during the out-of-school time hours. Appended are a demographic table, methods, references, and resource contact list.