The ability to estimate vehicle speed and stopping distance accurately is important for pedestrians to make safe road crossing decisions. In this study, a field experiment in a naturalistic traffic environment was conducted to measure pedestrians’ estimation of vehicle speed and stopping distance when they are crossing streets. Forty-four participants (18–45 years old) reported their estimation on 1043 vehicles, and the corresponding actual vehicle speed and stopping distance were recorded. In the speed estimation task, pedestrians' performances change in different actual speed levels and different weather conditions. In sunny conditions, pedestrians tended to underestimate actual vehicle speeds that were higher than 40 km/h but were able to accurately estimate speeds that were lower than 40 km/h. In rainy conditions, pedestrians tended to underestimate actual vehicle speeds that were higher than 45 km/h but were able to accurately estimate speeds ranging from 35 km/h to 45 km/h. In stopping distance estimation task, the accurate estimation interval ranged from 60 km/h to 65 km/h, and pedestrians generally underestimated the stopping distance when vehicles were travelling over 65 km/h. The results show that pedestrians have accurate estimation intervals that vary by weather conditions. When the speed of the oncoming vehicle exceeded the upper bound of the accurate interval, pedestrians were more likely to underestimate the vehicle speed, increasing their risk of incorrectly deciding to cross when it is not safe to do so.