During 1916 Ernst Ludwig Kirchner created a group of landscape paintings, based on his experiences at the Kohnstamm Sanatorium in Königstein, which were more symbolic in character than his previous landscapes. This essay shows that contact with Carl and Thea Sternheim, who encouraged a reengagement with Vincent van Gogh’s paintings and letters, played a role in this change. Kirchner’s recognition of how Van Gogh could express an affect through his painting was reinforced by Dr. Kohnstamm’s writings about empathy’s role in artistic expression. Artistic practice and aesthetic theory were joined in representations of Jena done during Fall 1916 in which Kirchner transformed the landscape through formal means into symbols of his emotional relationship to that space.