For 15 years, scholars have written that the dawn of accessibility-based transportation planning has arrived (e.g., Cervero, Rood, and Appleyard, 1999; Litman, 2013). The motivations for accessibility-based transportation planning are many, spanning all three branches of sustainability planning—environmental, social, and economic—and extending beyond sustainability-focused planning into other fields and more traditional sub-fields within planning. Yet mobility continues to dominate transportation planning in practice and in the literature (e.g., Bartholomew, 2009; Levine et al., 2012; Martens, 2006). The reasons for this are twofold. First, those benefitting from accessibility-based planning lack political clout. Secondly, accessibility 1 “is a theoretical construct based on the somewhat obtuse notion of ‘opportunities’” (Cervero, Rood, and Appleyard, 1999, p. 1277), while mobility is a more straightforward concept. Further limiting the potential implementation of accessibility planning is the fact that linkages between theory and application have not been considered beyond the urban versus rural distinction (e.g., Farrington and Farrington, 2005) and the needs of a growing senior population (e.g., Alsnih and Hensher, 2003). This issue is particularly vital to transportation planners in “shrinking” or “legacy” cities such as Detroit, Buffalo, and Cleveland. In such cities, increased competition for limited resources constrains planners’ ability to pursue accessible transportation options. Compounding this is the fact that decreasing population density limits the efficiency of public transportation as a whole (Schwanen and Mokhtarian, 2005). Finally, issues of social inequality challenge planning efforts in general in some shrinking cities, particularly in the Rust Belt (i.e., Galster, 2012), but elsewhere as well (i.e., Silver, 1984). The goal of this paper is to synthesize applications and knowledge gaps in the accessibility-based transportation planning literature in order to apply them specifically to a shrinking city context. Issues of accessibility apply to shrinking cities across economic, social, and environmental spheres.