Urban highways are unique windows from which to grasp a city’s identity. They can however be responsible for the fragmentation of cities and the degradation of their adjacent living environments. As many urban highways are aging, concerns about their redevelopment, upgrading or dismantling are emerging in many cities of the World. By examining the meaning as well as the opportunities offered by urban gateway corridors, the book attempts to offer a unique perspective on issues related this emerging landscape and transportation issue. More specifically, the book aims to describe the innovative approach to landscape infrastructure planning that was used for the YUL-MTL: Moving Landscapes initiative held in Montreal. Over two years, this initiative combined a design competition and a workshop with collaborative efforts between 20 public agencies to rethink a 17 km stretch of Montreal’s Autoroute 20 gateway corridor. Linking the downtown area to Montreal-Trudeau international airport, the corridor is mainly composed of transport infrastructures and industrial wastelands in dire need of revitalization along with residential areas.Overall, the book shows how the consideration of the landscape when it comes to development projects offers not only a rich contextual knowledge from a transversal and multidisciplinary perspective but also becomes a vector for the coherent planning of infrastructures and their integration within adjacent territories and within the city.