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This paper presents the outcomes from a joint research project that aims to develop a smartphone application/online platform to model the most thermally comfortable active transport route to a planned destination using heat information and tree shading (Shadeway). Here, we provide a summary of our systematic review of academic literature and applications from the Google Play and Apple App Store, to identify current knowledge about personal adaptation strategies when navigating travel in cities during high temperatures. The review identifies that there is a lack of attention regarding the use of smartphone applications to address urban thermal comfort for active transport by government and private industry. We then present the initial results of original research from three community focus groups and an online survey that elicited participants’ opinions about Shadeways in the City of Greater Bendigo (CoGB), Australia. The results clearly show the need for better management of Shadeways in CoGB. For example, 52.3% of the routes traveled by participants suffer from either no or poor levels of shading, and 53 of the shaded areas were located along routes that also experience heavy traffic, which can have an adverse effect on perceptions and actual safety. It is expected that this study will contribute to improve understanding of the methods used to identify adaptation strategies to increasingly extreme temperatures.