The Randolph Caldecott Medal is awarded annually by the Association for Library Service to Children (ALSC), a division of the American Library Association (ALA). Charged with identifying and honoring the most distinguished American picturebooks annually, the ALSC Board of Directors first awarded the Caldecott Medal in 1938. This article presents a content analysis of diversity representations of illustrators, authors, and main characters in Caldecott books since the inception of the award. The authors' findings reveal a series of changing maps that may reflect cultural messages about the time periods in which these books were created. Just as topographical maps reflect the forces that have shaped the land, this analysis hints at the forces--political, cultural, and social--that have shaped the Caldecott landscape. The authors compiled a database of all 337 Caldecott books. All 337 books were coded for both illustrator and author race/ethnicity as well as the race/ethnicity of main characters. When the authors examined the Caldecott books by decade, they discovered a layered pattern of information. If one looks at the decades as maps that provide insight into forces that can shape a landscape, one can infer the values and beliefs that are essential foundations to literature published during the time period. Looking across the decades uncovered peaks and valleys of the Caldecott terrain.