Walking is being promoted for health and transportation purposes across all climatic regions in the US and beyond. Despite this, an uncomfortable microclimate condition along sidewalks is one of the major deterrents of walking, and more empirical research is needed to determine the risks of heat exposure to pedestrians while walking. This study examined the effect of street trees and grass along sidewalks on air temperatures. A series of thermal images were taken at the average heights of adults and children in the US to objectively measure the air temperatures of 10 sidewalk segments in College Station, TX, USA. After controlling the other key physical environmental conditions, sidewalks with more trees or wider grass buffer areas had lower air temperatures than those with less vegetation. Children were exposed to higher temperatures due to the greater exposure or proximity to the pavement surface, which tends to have higher radiant heat. Multivariate regression analysis suggested that the configuration of trees and grass buffers along the sidewalks helped to promote pleasant thermal conditions and reduced the differences in ambient air temperatures measured at child and adult heights. This study suggests that street trees and vegetated ground help reduce the air temperatures, leading to more thermally comfortable environments for both child and adult pedestrians in warm climates. The thermal implications of street landscape require further attention by researchers and policy makers that are interested in promoting outdoor walking.