The current condition of the nation’s transportation system is of great concern to State Departments of Transportation. Currently, funds in many state transportation budgets are depleting. Nowadays, State DOT officials together with researchers are exploring various transportation financing approaches and they are considering the utility, merits, challenges, and impacts of these approaches. A major financing approach being considered relies on the collection of tolls on existing toll roads and on roads on which tolls are not presently collected. Recent technology advancements in Open Road Tolling and All-Electronic Tolling have provided State DOTs with the opportunity to consider expanding the use of toll revenue to finance transportation investments. These two types of tolling technologies appeal to motorists by allowing them to maintain their current highway speed while going through a toll plaza. In addition, many State DOT officials now view toll based approaches as viable “user fee” based strategies together with other alternative approaches such as the fuel tax and sales tax. Central to this research is a case study of the Boston Metropolitan area. The case study includes the formulation and preliminary evaluation of toll based financing approaches potentially suitable for consideration in Massachusetts. The approaches include increases to existing tolls and placing tolls on selected roadways not currently tolled. The evaluation includes estimates of changes in demand and anticipated revenues associated with these toll based approaches. It is expected that the results of this research will be of interest to State DOT officials in Massachusetts and other states.