Drawing maps for historians involves a number of distinct challenges. The historical cartographer must grapple not only with geological changes over time, but geographical ones, from human-cultural to physical, and from political to spatial. Original manuscripts must be read with close attention toward extracting geographical data, map sources must be vetted, and design challenges must be resolved. Furthermore, many of the antiquarian sources that are used to create current-day maps of historical times have unique scales, projections, and senses of place—all of which present complications that need to be overcome when creating historically based maps for publication. This thesis describes some of the quagmires that the historical cartographer encounters on a regular basis, and details methods for avoiding them. Using maps drawn by the author as source materials, techniques for creating historically cognizant, technically accurate, and elegant maps are examined and described as parts of the process of illustrating historians’ manuscripts. Ultimately, the goal of the historical cartographer is to create maps that provide readers with an easily graspable graphic methodology for understanding the arguments presented in the text. When this is done well, the maps support the legitimacy of the historian’s research and offer a clarity of vision that might otherwise be difficult with words alone.