Vehicle-to-barrier (V2B) communication is a recently introduced vehicular communication technology, which aims to facilitate wireless interactions between vehicles and roadside barriers in next-generation vehicular systems. V2B systems will help mitigate single-vehicle, run-off-road (RoR) crashes, which account for a large proportion of roadside crash fatalities. RoR crashes may not be addressed by existing vehicular communication systems, such as vehicle-to-vehicle and vehicle-to-infrastructure. Today, orthogonal frequency division multiplexing (OFDM) is vastly utilized in vehicular communication systems. Thus, there is a need to understand the signal characteristics of the channel, especially just before and during a crash. To this end, the first real-world crash test measurement results for OFDM-based V2B communications are presented herein based on two crash tests. These tests include a bogie vehicle crash test into a soil embedded post at an impact velocity of 27 mph and a Toyota sedan crash test into a concrete curb with an impact velocity of 15 mph, conducted at the outdoor proving grounds of Midwest Roadside Safety Facility (MwRSF), Lincoln, Nebraska. Experiment results illustrate the characteristics of V2B OFDM communication during vehicle encroachment and crash. The results highlight the adverse effects of vehicle encroachment and crash on OFDM signals, in terms of average received signal strength, peak to average power ratio, error vector magnitude, and phase error.