The twenty-first century is the era when populations of cities will exceed rural communities for the first time in human history. The population growth of cities in many countries, including those in transition from planned to market economies, is putting considerable strain on ecological and natural resources. This paper examines four central issues: (a) the challenges and opportunities presented through working in jurisdictions where there are no official or established methods in place to guide regional, ecological and landscape planning and design; (b) the experience of the author’s practice—Gillespies LLP—in addressing these challenges using techniques and methods inspired by McHarg in Design with Nature in the Russian Federation in the first decade of the twenty-first century; (c) the augmentation of methods derived from Design with Nature in reference to innovations in technology since its publication and the contribution that the art of landscape painters can make to landscape analysis and interpretation; and (d) the application of this experience to the international competition and colloquium for the expansion of Moscow. The text concludes with a comment on how the application of this learning and methodological development to landscape and ecological planning and design was judged to be a central tenant of the winning design. Finally, a concluding section reflects on lessons learned and conclusions drawn.