Over the last four years, the Afterschool Alliance and MetLife Foundation have worked together to identify exemplary, and often lesser-known afterschool programs across the nation. For the past two years, efforts have focused on finding innovative afterschool programs serving middle school students. This focus was developed to address the need for new and innovative ways to engage adolescents during a crucial juncture in their lives, when they are still developing as both students and individuals. Some middle schoolers are mature for their age and ready for the transition to high school, while others still yearn for the comfort of elementary school. The question beckons: How do you deal with a population of students who are rapidly growing as individuals but are still unsure of their identity among peers and their strengths in the classroom? In 2011, the partners attempted to answer this question by identifying afterschool programs that are successfully engaging middle school students and toeing the line between providing a safe, nurturing environment while also affording youth a space to explore new interests and drive their own learning. The Afterschool Alliance and MetLife Foundation accomplished this through a competitive awards program that attracted more than 300 nominations from programs nationwide. With the help of external reviewers, the pool of nominees was narrowed down to 20 programs to be featured in issue briefs. Five of those programs were then selected as MetLife Foundation Afterschool Innovators. This year, each of the MetLife Foundation Afterschool Innovators received a $10,000 award to sustain and expand their work. This paper features in-depth case studies of the five programs selected as 2011 MetLife Foundation Afterschool Innovator Award winners which include: (1) Kids Rethink New Orleans Schools (New Orleans, LA); (2) Higher Achievement (Washington, D.C.); (3) Urban Arts/Project Phoenix (Oakland, CA); (4) 21st Century PASOS (Gettysburg, PA); and (5) America SCORES (Chicago, IL). Hopefully, these case studies will help other programs across the country learn from each program's achievements and apply the lessons learned by these Innovators in their own programs.