What Could Joshua Chamberlain See at Gettysburg? is a project that re-examines the decisions made during the Battle of Little Round Top in 1863 using digital humanities methods. Chamberlain is well known for ordering a bayonet charge that helped the Union line secure Little Round Top. Until now, Chamberlain’s line of sight during the battle has not been investigated using digital tools. Digital tools create data that supplements the pre-existing historical narrative of that fateful day. One of the main objectives is to create data visualizations that show us not only what Chamberlain could actually see from his vantage point, but also uncover the external influences and forgone decisions that affected the outcome at Little Round Top. The visualization software Gephi was used to create digital networks of Chamberlain’s overall correspondence based on over 500 original letters. Gephi enabled us to repurpose the original letters to gain insight into the humanistic side of Chamberlain’s decisions during the battle. GIS, a mapping software, was then used for georeferencing and geoprocessing. Georeferencing compares the accuracy of the historical maps Chamberlain and his line used to modern topo maps. Using geoprocessing tools, it was possible to create an image that shows Chamberlain’s visibility at Little Round Top, which suggests that the southern region of Little Round Top was the least visible from Chamberlain’s position. This limited visibility challenges Chamberlain’s strategy and could determine if his success in the environment of Little Round Top can be attributed to good fortune or careful planning.