Urban planning and design action in the face of rapid global urbanization and attendant changes in the urban environment urgently needs holistic indices of environmental quality. The use of vegetation changes to monitor urban environmental quality appears promising, thanks to recent advances in the remote sensing of greenery. The utility of remotely sensed vegetation data to monitor the urban physical environment is well known. Recently, Emmanuel (1997) demonstrated that such data could also mirror the social and demographic trends in cities. This paper explores the urban design/planning implications of using vegetation change as indicator of urban environmental trends. The case study is based on research work carried out in Detroit, USA, where urban decay in recent years has lead to significant greening in the heart of the city. A hypothesis of urban environmental transition is proposed.