This study aims to examine the relationship between urban densification and pedestrian thermal comfort at different times of the year, and to understand how this can impact patterns of activity in downtown areas. The focus of the research is on plazas in the urban core of downtown Tempe, given their importance to the pedestrian landscape. With that in mind, the research question for the study is: how does the microclimate of a densifying urban core affect thermal comfort in plazas at different times of the year? Based on the data, I argue that plazas in downtown Tempe are not maximally predisposed to pedestrian thermal comfort in the summer or the fall. Thus, the proposed intervention to improve thermal comfort in downtown Tempe’s plazas is the implementation of decision support tools focused on education, community engagement, and thoughtful building designs for heat safety.