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Social studies teachers face a number of disciplinary challenges--for instance, insufficient geographic knowledge, fewer opportunities for critical analysis amid shrinking instructional time--and, in terms of confronting discrimination and disparity, an increasingly racially segregated society. Teachers can, however, make excellent use of historical resources and modern mapping tools to empower students in their analysis of the Jim Crow era and segregation in American daily life. This article describes the use of The Negro Motorist Green Book, a guide produced from 1937 to 1963 for African-American drivers which detailed American businesses which catered to black travelers. Using the data from these books, students can create critical maps detailing both the state off American segregation and the efforts, through the 20th century, to subvert it.