Past studies have highlighted the importance of risk assessment and management in construction projects and transportation industry, and have identified cost and time as the most important risks that transportation professionals want to understand and manage. The main focus of this study is to comprehensively analyze transportation construction risk drivers and identify the correlation of the significant risk drivers with project characteristics, cost growth, schedule growth, and project contingency. This study has adopted 31 relevant and significant programmatic and project-specific risk drivers from different past studies. These risk drivers have been analyzed and evaluated using survey responses from professionals in the context of highway transportation projects. Risk assessments including rating of the encountered risk drivers and their correlation with project characteristics have been carried out within the context of highway construction projects in the United States. Correlations of the construction project performance or risk measures, cost growth percentage, and schedule growth percentage, with the rating values of identified risk drivers values have enabled a better understanding of the impacts of risks and the risk assessment process for highway transportation projects. The impact of significant risk drivers on reported construction cost contingency amounts has also been analyzed. The purpose of this effort was to assess impact of ratings for cost impact, schedule impact, and relative importance of the identified risk drivers on contingency amounts. Predetermined method is the common way to calculate contingency amount in transportation projects. In this study parametric modeling has been used to analyze the relationship between predetermined contingency amounts in transportation projects with perceived risk rating values in order to understand how the expert judgments regarding risk ratings can be used in determination of contingency amounts.