In order to preserve and ensure the vitality of freedom and democracy in democratic societies, it is important that citizens reflect deeply on the meaning of freedom and the conditions necessary to sustain it. The idea for this volume arose from discussions at the February 2019 annual meeting of the Georgia Philosophical Society held at Mercer University on the theme of "Freedom and Society," and drafts of many of the chapters were first presented there. Including contributions from both early-career and well-known scholars, the chapters are tied together by questions about the nature of political freedom and autonomy in democratic societies and about the ways in which the enactment of democratic freedom depends on awareness of and engagement with freedom's underlying conditions. These conditions include social responsibility, creative innovation, and strong democratic institutions. Other recurring themes in the volume include the pitfalls of atomistic models of autonomy and the importance of giving due consideration to intersubjectivity, embodiment, and plurality as integral elements of a free society. Countering models centered exclusively on negative freedom, (i.e. freedom from constraints imposed by others), several chapters highlight the crucial roles of social responsibility and creativity in confronting obstructions to freedom, such as systemic racism and other challenges currently facing democracies. Finally, several chapters emphasize the fundamental importance of strong and just democratic institutions as the primary means of reliably expressing the will of the people.