This publication highlights lessons learned by participants at the May 2006 AYPF field trip to Philadelphia about the best practices the city uses to sustain its comprehensive out-of-school time system. In May of 2006, the American Youth Policy Forum (AYPF) led a field trip to Philadelphia, Pa., in an effort to expose Washington, DC policymakers to the unique, comprehensive out-of-school time (OST) programming system that Philadelphia has created and successfully sustained. Visitors included staff from the US Departments of Education and Labor, the District of Columbia public school system, youth programs that focus on issues such as juvenile justice, employment, and education, and representatives from intermediaries that work with cities and other local entities. The participants shared an interest in learning how a city with high rates of youth violence, crime, drug use, and academic failure, coupled with relatively low rates of high school graduation, employment, and college entry, is able to engage various systems and programs in successfully working together to increase opportunities and improve outcomes for all of the city's youth.