As cities develop and urbanize, and space becomes increasingly valuable, additional pressures are placed on all systems including transportation. Road pricing has been used to generate revenue, mitigate congestion, and reduce pollution. However, implementing road pricing schemes has been difficult, given its contentious nature. This study begins by providing a brief literature review of road pricing and highlighting lessons from key road pricing schemes that have emerged throughout the last twenty years. While previous studies have been explored extensively for their successes and limitations, the Bay Bridge has been comparatively understudied. The Bay Bridge showcases atypical characteristics that have influenced construction and pricing structures throughout its history. Given multiple case studies, and a more in-depth knowledge of the Bay Bridge, the current study identifies lessons that can be applied for the Bay Bridge as it continues to evolve and for the broader future of road pricing internationally.