This article investigates how experimental forms of urban mapping can reveal the particularity of places in non-standard urban situations with the intention of moving beyond the reductivism of still-dominant modernist modes of mapping and associated forms of planning. In order to do so, it reports on the emergence of a methodology involving transect walks, with the purpose of mapping the peculiarities of cultural landscapes. The study is located in cities and communities in the Arctic that are undergoing rapid transformation and are in urgent need of new conceptual approaches capable of enabling future thinking and strategic action. The article specifically asks how such a methodology works to includes th eephemeral and emergent, but also digital, dimensions of urban landscapes, and results in a complex reflexive method of critically reading and writing, of moving and locating, of seeing and picturing place mapping.