Connected vehicle (CV) technology aims to improve drivers’ situational awareness through audible and visual warnings displayed on a human–machine interface (HMI), thus reducing crashes caused by human error. This paper developed a driving simulator test bed to assess the readability and usefulness of the Wyoming CV applications. A total number of 26 professional drivers were recruited to participate in a driving-simulator study. Prior to driving the simulator, the participants were trained on both the concept of CV technology and the developed CV applications as well as the operation of the driving simulator. Three driving simulation scenarios were designed. For each scenario, participants drove two times: one with the HMI turned on and another one with the HMI turned off. After driving the simulator, a comprehensive revealed-preference survey was employed to collect the participants’ perceptions of CV technology and Wyoming CV applications. Results show that the Wyoming CV applications were most favored under poor-visibility driving conditions. Among the Wyoming CV applications, forward collision warning and rerouting applications were experienced as the most useful. Approximately 89% of the participants stated that the Wyoming CV applications provided them with improved road condition information and increased their experienced safety while driving; 65% of the participants stated the CV applications and the HMI did not introduce distraction from the primary task of driving. Finally, this paper concludes that the design of CV HMI needs to balance a trade-off between the readability of the warnings and drivers’ capability to safely recognize and timely respond to the received warnings.