Woodruff traveled to Paris from 1927-1931, joining a group of expatriated African American artists and intellectuals. In Paris, he attended classes at the Académie Scandinavia and Académie Moderne, and visited Claude Monet’s memorial exhibition at the Jeu de Paume. Woodruff spent his time visiting various regions of France painting academic landscapes and landmarks and experimenting with Cubism. In 1928, Woodruff traveled along the Eure River in the Beauce Valley, known as the location of the Chartres Cathedral. He painted the famous gothic cathedral and several scenes depicting the ancient waterway and surrounding medieval structures between 1928 and 1929. Medieval Chartres is among this body of work, and was exhibited alongside other similar scenes in a 1929 Harmon Foundation annual exhibition in New York, which later traveled to Spelman College.