In 1921, Rakeman joined the Department of Agriculture, which at that time housed the Bureau of Public Roads (BPR) - predecessor of the present Federal Highway Administration. During his career BPR, he painted exhibits for the Good Roads meetings, state fairs, and expositions such as the Brazilian Exposition (1922), the Century of Progress in Chicago (1933), an Overseas Exposition in Paris, the Golden Gate Exposition in San Francisco (1939) and the New York World's Fair (1940). In addition, he completed the series of 109 paintings depicting historic American roads, trails, and highways.