This collaborative essay invites historians to consider radical walking tours' potential as a dynamic strategy for critiquing liberal understandings of crime in urban settings. The authors examine two very different cities—New York City and East St. Louis, Illinois—in which existing tours have missed opportunities to redefine the legal and the criminal. Rebecca Amato notes how sensationalist crime tours in New York have obscured more challenging legal histories of gentrification and property laws that allow for displacement of poor immigrant neighborhoods. Jeffrey Manuel then describes how certain crimes, notably crimes committed by corporations, are covered up in East St. Louis's rare tours and suggests how tours could be used to reveal the ways in which corporations and governments use the law to harm people and the environment. In each case, existing tours either downplay the contemporary built environment or treat it as mere background to the historical narrative. To conclude the essay, the authors offer four suggestions for incorporating radical walking tours of the law into classrooms and public history projects.