The greenway movement in Singapore began in the late 1980’s as a proposal for an island-wide network of green corridors. The paper traces the conceptualization, planning strategy and implementation of this greenway network. The capitalization of under-utilized land along drainage channels and beside carriageways for pilot greenway projects ensured government backing for the projects. The challenges faced in implementing the projects and the solutions taken to advance the greenway concept are discussed. Garnering public support for the completed sections generated resources and conferred additional flexibility to the land allocation process, allowing the concept to evolve. Strategic partnership with key land-use agencies and the overview of a national Garden City Action Committee for conflict resolution facilitated the process. Lessons are drawn from the implementation of the pilot projects to inform subsequent greenway development efforts, enhancing the usage and multi-functional capacity of the greenways. The Singapore experience provides a model for greenway planning and implementation for other rapidly urbanizing cities in Asia.