Valley Park Middle School (VPMS) in Valley Park, MO, has the unique designation of being a not-so-secret gem in St. Louis County. The middle school shares its campus with the elementary and high school, creating opportunities to collaborate and work together to build a school district that not only shines academically, but also focuses on developing character in students at every level of schooling. Parents, community, and school board members are proud of the fact that students get the best of what a small private school has to offer. In 2003, VPMS was randomly selected to participate in a federal grant program (Missouri Show Me CharacterPlus Implementation Study) designed to develop strong character education programs in schools to help improve climate and academics. For the past 13 years, VPMS has lived up to the challenge and has become a model for other schools to emulate. This article describes how VPMS has faced and managed new challenges and initiatives as they continue to find ways to emphasize and include character education into all programs within the school culture.