We paired an urban field game with a discussion of the past, present, and future of escape in the city. Brent D. Ryan, Associate Professor of Urban Design and Public Policy at MIT; Jeffrey Shumaker, Deputy Chief Urban Designer for the City of New York; Elihu Rubin, Assistant Professor of Architecture and Urbanism at Yale University; and Gabrielle Esperdy, Associate Professor of Architecture at the New Jersey Institute of Technology, examined the fluctuating perceptions of the city’s relationship to escape—tracking its evolution from 19th-century land of opportunity, to 20th-century land of urban flight, and on to today’s megalopolis as a place that people escape to, from, and within.