Walking is essential for the health and well-being of communities as well as meeting environmental challenges of the 21st Century. There have been significant research contributions in recent decades to understanding factors that can influence the likelihood of citizens choosing active travel modes, with great advances in understanding the built environment, particularly macro-scaled urban factors such as land-use mix, population density, and street patterns. So why are people <i>still</i> not walking? And is there anything we can do to try to change this? To answer these questions, this paper explores walking environment assessment approaches using a trans-disciplinary narrative approach, touching on multiple critical disciplinary knowledge areas. We find that while much of the research into the built environment’s influence on walking has made positive contributions in helping identify areas of cities that discourage active travel, the capacity to improve these areas has been limited. While macro-scaled factors commonly considered in ‘walkability’ analysis are highly influential to mode choice, unless working on green-field development, these factors may require re-zoning private land, substantial demolition and renewal, and may be financially or politically infeasible and thus extremely difficult to change. There is a need to augment macro-scaled analysis with micro-scaled tools, and to establish multi-criterion spatio-temporal design decision support approaches drawing from emerging technologies to make informed, integrated and effective urban design changes. These methods applied at precinct and streetscape levels have the potential to make feasible improvements to the ‘walk-quality’ of the built environment and contribute to facilitating active travel.