Background: Principals are key to the promotion of physical activity (PA) in schools. The purpose of this study was to understand how school principals’ PA values, behaviors, and individual and school characteristics were associated with the presence of an active school. Methods: A representative sample of 1019 school principals in the United States was surveyed. Survey items addressed principals’ values and behaviors associated with PA, individual and school demographic factors, such as years of experience and school level, and a single item asking whether principals perceived their school to be an active school (ie, provides students with opportunities to be physically active before, during, and after the school day). Significant variables from a cross-tabulation and chi-square analysis were added to a hierarchical logistic regression model to assess the predictive properties of principal values and behaviors as they relate to the presence of an active school. Results: Approximately half of principals (47%) reported having an active school. The model significantly predicted the presence of an active school but accounted for only 6.6% of the total variance. Although values toward PA and more frequent personal PA behaviors were associated with the presence of an active school within the cross-tabulation and chi-square analysis, neither variable emerged as a significant predictor in the regression model. Conclusions: Principals’ personal PA values and behaviors contribute to the presence of an active school, but other variables, including years of experience and school contextual factors, are more powerful predictors.