Research indicates many children today spend little time outdoors exploring the natural world and a great deal of time inside viewing the television or playing video games (Jerald, 2009; Robinson, 2010) which can lead to poor social development, childhood obesity, and a lack of feeling connected to the environment. One instructional tool being used by some schools to address these rising concerns is a school garden. School gardens can provide an opportunity for students to experience learning through authentic, real-world application. This qualitative multi-case study explores three school gardens in the harsh growing climate of Southwest Montana. Triangulation of field notes, interviews, and multiple artifacts identified challenges encountered and successes realized as well as identifying characteristics found in a successful school garden program. Despite the unique characteristics of each school garden, evidence suggests successes realized far exceed challenges encountered across cases. Recommendations provide guidance for design and implementation of school gardens and suggestions for further research are provided.