Mitigating heat is a vital ecosystem service of trees, particularly with climate change. Land surface temperature measures captured at a single time of day (in the morning) dominate the urban heat island literature. Less is known about how local tree canopy and impervious surface regulate air temperature throughout the day, and/or across many days with varied weather conditions, including cloud cover. We use bike-mounted air temperature sensors throughout the day in New Haven, Connecticut, USA, from 2019 to 2021 and generalized additive mixed models across 156 rides to estimate the daily variation in cooling benefits associated with tree canopy cover, and warming from impervious surface cover in 90 m buffers surrounding bike observations. Cooling is inferred by subtracting the bicycle-observed temperature from a reference station. The cooling benefits from tree canopy cover were strongest in the midday (11:00–14:00, −1.62 °C), afternoon (14:00–17:00, −1.19 °C), and morning (8:00–11:00, −1.15 °C) on clear days. The cooling effect was comparatively smaller on cloudy mornings −0.92 °C and afternoons −0.51 °C. Warming from impervious surfaces was most pronounced in the evening (17:00–20:00, 1.11 °C) irrespective of clouds, and during cloudy nights (20:00–23:00) and cloudy mornings 1.03 °C 95 % CI [1.03, 1.04]. Among the hottest observed days (top 25th percentile of reference station daily maxima), tree canopy was associated with lower temperatures on clear afternoons −1.78 °C [-1.78, −1.78], cloudy midday −1.17 °C [-1.19, −1.15], clear midday −1.12 °C [-1.12, −1.11]. We add a broader spectrum of weather conditions by explicitly including clouds, and greater temporal resolution by measuring throughout the day to bike-based urban heat research. Future mobile sampling campaigns may broaden the spatial extent with more environmental variation, representing an opportunity for public science and engagement.