Speeding has been and continues to be a major contributing factor to traffic fatalities. Various transportation agencies have proposed speed management strategies to reduce the amount of speeding on arterials. While there have been various studies done on the analysis of speeding proportions above the speed limit, few studies have considered the effect on the individual's journey. Many studies utilized speed data from detectors, which is limited in that there is no information of the route that the driver took. This study aims to explore the effects of various roadway features an individual experiences for a given journey on speeding proportions. Connected vehicle trajectory data was utilized to identify the path that a driver took, along with the vehicle related variables. The level of speeding proportion is predicted using multiple learning models. The model with the best performance, Extreme Gradient Boosting, achieved an accuracy of 0.756. The proposed model can be used to understand how the environment and vehicle's path effects the drivers' speeding behavior, as well as predict the areas with high levels of speeding proportions. The results suggested that features related to an individual driver's trip, i.e., total travel time, has a significant contribution towards speeding. Features that are related to the environment of the individual driver's trip, i.e., proportion of residential area, also had a significant effect on reducing speeding proportions. It is expected that the findings could help inform transportation agencies more on the factors related to speeding for an individual driver's trip.