Background: The association between maternal depression and child negative behavior outcomes has been well established in the literature. However, understanding how maternal depression is associated with child behaviors will have important implications for research and intervention strategies. Objective: We used samples from two distinct family contexts: urban, middle-class families (N = 454); and rural, low-income families (N = 240), to compare the impact of family rituals and maternal depressive symptoms on child externalizing behaviors. We also examined the impact of maternal depressive symptoms on family rituals. Methods: Structural equation modeling and multiple group analyses were conducted. Child age, child gender, mother age, mother education, mother partner status, family income, and family size served as control variables. Indirect effect tests and incremental validity tests were performed. Results: Depressive symptoms were linked to externalizing behaviors in both samples. The impacts of family rituals on child externalizing behaviors were more context-specific. For urban, middle-class families, vacations played a particularly helpful intermediate role. Also, in these families, maternal depressive symptoms were associated with less involvement in religious holidays. For rural, low-income families, involvement in annual celebrations was associated with less child externalizing behaviors, although maternal depressive symptoms did not impact involvement in any family rituals. Conclusions: Results suggest that family context matters in determining the impacts of maternal depression on the practice of family rituals, as well as the benefits of family rituals for child behaviors, and that certain family rituals can do more than others to reduce child externalizing behaviors (e.g., vacation).