Despite substantial evidence that resources and outcomes are transmitted across generations, there has been limited inquiry into the extent to which anti-poverty programs actually disrupt the cycle of bad outcomes. We explore how the effects of the United States' largest early childhood program, Head Start, transfer across generations. We leverage the rollout of this federally funded, means-tested preschool program to estimate the effect of early childhood exposure among mothers on their children's long-term outcomes. We find evidence of intergenerational transmission of effects in the form of increased educational attainment, reduced teen pregnancy, and reduced criminal engagement in the second generation.