Background: Little empirical research examines relations among the quality of both mothers' and fathers' social emotional and linguistic support of toddlers across multiple parent-child interaction contexts. Objective: The current study investigated the influence of parent gender (mother vs. father) and activity setting (structured task vs. free play) on parenting quality, toddlers' engagement and play behaviors, and parent-toddler language use. Methods: Sixty predominantly middle-class, two-parent families with toddlers participated. Mother-child and father-child dyads were observed in a laboratory setting during structured and free play sessions. Results: There were significant main effects, controlling for child age, of activity setting on parenting quality (cognitive scaffolding and negative behaviors), children's engagement with parents, play behaviors, and parent and child language use. There was no main effect of parent gender on the parent and child variables, except for parent language variables. Conclusion: Overall, free play rather than the structured task setting was associated with more favorable child and parent interactions, play, and language use. Implications for future research and practice are discussed.