The purpose of this collective case study was to explore how successful urban choral educators use contextual knowledge to inform pedagogical practice. With choirs in nine of a large midwestern city's demographically varied residential neighborhoods, a children's choir organization provided a research setting that offered a unique view of urban teachers' contextual knowledge. The study's ethnically diverse participants taught in multiple classrooms each week, providing opportunities to explore how the same teacher responded to more than one demographic setting. Participants relied upon knowledge of learners, knowledge of context, and personal practical knowledge to successfully navigate the urban environment. Findings were interpreted in light of Geneva Gay's five essential elements of culturally responsive teaching to illustrate how the teachers enacted contextual knowledge through culturally responsive practice. Implications for music teacher education are discussed based on the findings.