This paper examines the role of geopolitics, including armed conflict, in family farming. Drawing on critical approaches to geopolitics in geography and anthropology, we situate the dynamics of family farming in the context of multiscalar struggles over territory and political sovereignty. Our historically and geographically situated approach shows how geopolitical positionality engenders vulnerabilities as well as political potential for alternative development by shaping labor and gender dynamics in farming households. Empirically, our research provides an illustrative example of the Baltic states, especially Latvia and Lithuania, which have been situated within geopolitical fault lines for centuries. Focusing on four different historical periods, we demonstrate how the dynamics of family farming in the Baltic states—characterized by the persistence of smallholder family farms and specific land ownership patterns with women owning almost half of farms—are partly a result of the multiscalar geopolitics manifesting itself in violent colonial histories. Our analysis also reveals how various geopolitical power interplays in borderlands can lead to devastating consequences, while simultaneously creating pathways for alternatives to the capital-intensive, environmentally destructive, and socially exploitative corporate food regime. Overall, our research underscores the complex ways in which geopolitical (in)security undergirds labor and gender in farming households.