The dangerous work environment in the construction industry and the inherent high risks associated with construction work make it the focus of safety training and regulations. Highway construction and maintenance has unique hazards but seemingly less directly applicable safety standards, regulations, and programs. Department of Transportation (DOT) employees working in highway maintenance are exposed to a variety of unique hazards specifically associated with their work and not relating to the adjacent traffic. Yet, highway construction and maintenance work has not received sufficient attention in terms of safety research and programs. The lack of safety training and education in highway construction and maintenance work leaves a significant portion of DOT employees prone to different work-related hazards that can be avoided with additional safety awareness. As part of the efforts of the Kentucky Transportation Cabinet (KYTC) to improve safety of their employees, the study describes the design, implementation, and evaluation of a pre-task safety briefing toolbox. By analyzing recordable incidents of KYTC maintenance employees and identifying frequent hazards present within their typical work operations and the causes behind the frequent incidents, the final product of design phase is a toolbox that is relatable and relevant to KYTC maintenance crews. The toolbox presents these hazards along with incidents causes and the appropriate safety practices to avoid or mitigate the associated risk. The goal of this safety toolbox is to improve safety awareness of KYTC maintenance crews. The second part of the study is a comprehensive systematic evaluation of the effectiveness of the toolbox. Three evaluation phases including reaction and knowledge evaluation, implementation evaluation, and behavior change evaluation were carried out to assess the effectiveness of the toolbox. With 22% improvement in workers safety knowledge, 23% improvement in workers hazards identification skills, and 33.24% increase in the likelihood of safe behavior, the results showed that pre-task safety toolbox talks can increase highway workers’ safety awareness, improve their hazards identification skills, and increase their safe behavior. In addition to serving an underserved audience of the construction workforce, this study contributes to the body of knowledge in different ways. First, it sheds the light on a significant underserved portion of construction workers and the unique hazards present in their work environment. Second, it presents the design, implementation, and evaluation of a data driven safety intervention that addresses the most frequent safety issues in highway maintenance operations. Finally, it presents an empirical trial to evaluate the effectiveness of a common practice used in the construction industry in a unique sector of the industry that has not received sufficient research efforts.