Anarchism and geography have a long and disjointed history, characterized by towering peaks of intensive intellectual engagement and low troughs of ambivalence and disregard. This paper traces a genealogy of anarchist geographies back to the modern development of anarchism into a distinct political philosophy following the Enlightenment. The initial rise of geographers’ engagement with anarchism occurred at the end of the 19th-century, owing to Élisée Reclus and Peter Kropotkin, who developed an emancipatory vision for geography in spite of the discipline’s enchantment with imperialism at that time. The realpolitik of the war years in the first half of the 20th-century and the subsequent quantitative revolution in geography represent a nadir for anarchist geographies. Yet anarchism was never entirely abandoned by geographical thought and the counterculture movement of the 1970s gave rise to radical geography, which included significant interest in anarchist ideas. Unfortunately another low occurred during the surge of neoliberal politics in the 1980s and early 1990s, but hope springs eternal, and from the late 1990s onward the anti-globalization movement and DIY culture have pushed anarchist geographies into more widespread currency. In reviewing the literature, I hope to alert readers to the ongoing and manifold potential for anarchist geographies to inform both geographical theory and importantly, to give rise to more practice-based imperatives where building solidarities, embracing reciprocity, and engaging in mutual aid with actors and communities beyond the academy speaks to the ‘freedom of geography’ and its latent capacity to shatter its own disciplinary circumscriptions.