Considerable research has demonstrated that substance use and delinquency during early adolescence can have long-term negative health consequences. As the correlates of these behaviors cross levels and contexts, it is likely that a social ecological approach will provide insight to inform community prevention. This approach informs the present study, which focuses on developing a multiple-method measurement strategy to examine associations among community risks, resources, and rates of early adolescent substance use and delinquency in 28 rural and small town communities. Measures include five domains of community risk, four domains of community resources, and population rates of early adolescent substance use and delinquency. Results demonstrated that several measures of context were significantly associated with community rates of adolescent substance use and delinquency, and different risks and resources appear important for different outcomes. Multiple associations were curvilinear, and interactions may also be important. Findings suggest that it may be worthwhile to create and test new intervention strategies that target community factors in the pursuit of prevention.