Maintaining and increasing canopy cover is frequently promoted as a strategy for mitigating excess heat in cities. However, the impact of changing tree cover on surrounding air temperatures is often unpredictable and can depend on tree species, size, shape, and location. In this study, we explore whether the removal of ash trees in one downtown neighborhood in Madison, Wisconsin affected surrounding air temperatures at small spatial scales (15 to 35 m). We used a bicycle-mounted temperature and radiation sensor to repeatedly record high-frequency observations along four transects. We observed no discernible difference between daytime air temperatures near locations surrounded by tree removals and temperatures at locations without any nearby tree removals. Overall, across the four clusters of streets that were monitored, proximity to mature ash trees did not correlate to reduced air temperatures. Attempts to model temperature as a function of surrounding land cover and street tree characteristics all had poor predictive power (R2 ranged from 0.01 to 0.54), and explanatory variables related to tree cover were never statistically significant. The finding that the removal of ash trees did not impact daytime air temperatures patterns at the neighborhood scale suggests that the most densely developed streets in Madison may not easily support sufficient canopy cover to experience tree-induced cooling, underscoring the importance of pursuing a variety of strategies to mitigate urban warming.