According to the framework outlined by the Forum for Youth Investment (FYI), the challenges faced by cities as they attempt to build citywide afterschool programming involve: (1) quality and continuity of programs; (2) sufficient capacity and resources; and (3) a climate that supports action and investment. The eight citywide afterschool programs featured here were implemented in: Denver, CO; New York, NY; San Diego, CA; Boston, MA; St. Louis, MO; San Francisco, CA; Los Angeles, CA; and Seattle, WA. The programs were chosen for inclusion in this report because they demonstrated different approaches to organizing a citywide afterschool initiative. Each description details the profile of the city and the afterschool programming needs of the community, key strengths of the program, lessons learned, and the major challenges faced by the program. For example, Denver’s afterschool initiative began in 1990 as a middle school magnet program that met with glowing reviews, spurring the development of school neighborhood centers to support individuals, agencies, and institutions committed to meeting community needs. Key strengths of the Denver program include the strong commitment of the public school system and the diversity of afterschool services offered. Lessons learned from the Denver afterschool program include the need for written program guidelines and the importance of neighborhood needs assessment analyses. One of the key challenges of the Denver program is to maintain a strong school-city partnership. Following the descriptions of the eight programs, appendixes include the Elements for Building Citywide Afterschool Initiatives, as well as an overview of the Cross-Cities Network. Notes, appendixes