The interdisciplinary field of historical geographic information systems (HGIS) took root and flourished at the Social Science History Association (SSHA) in the late 1990s and early 2000s. This essay first recounts the growth of HGIS at SSHA and beyond. It then considers challenges that GIS continues to pose for historians and other scholars, such as the unfamiliarity of its conceptual framework and the time and expense often involved in building HGIS databases. The bare-bones visual culture of Social Science History may inhibit submissions by HGIS scholars, whose work typically includes color maps. Yet the enduring methodological and interdisciplinary interests of SSHA members provide a strong basis for continuing involvement by historians who use GIS. The essay closes with new directions in HGIS scholarship, including study of empirical uncertainty, historical gazetteers, textual analysis linked to GIS mapping, and comparison of topology and topography.