Powered Two-Wheelers (PTWs) have significantly gained momentum in developing countries, specifically Latin American cities, due to their ease of use and inexpensive nature. Motorcyclists are vulnerable road users who heighten their risk when practicing illegal actions such as red-light violations, maneuvering, and driving in undesignated lanes. This research provides a video-based surrogate safety methodology into the behavioral aspects of PTW users within Mexico City, Mexico, and São Paulo, Brazil. Two signalized and two unsignalized intersections in each of the cities were selected, and hundreds of hours of video data were collected from on-site installed cameras and processed in automated software. Statistical models and comparative analyses between the cities were generated to measure motorcyclist behaviors according to a set of identified factors. Preliminary results show that helmet use is high, with 97.8% and 98.7% percentages incurred in Mexico and Brazil, respectively. Mexico City motorcyclists are 2.2 times more likely than those in São Paulo to perform risker activities. Regardless, riders in São Paulo pose a significant proportion in committing road safety violations (maneuvering) as 37.25% of motorcyclists consistently change lanes. These behavioral attributes allow for further research to address experimental mitigating actions that lessen the consequences of risky motorcycle travel.