The intended purpose of an intelligent transportation systems (ITS) project is to automate operations through device-to-device connectivity. These devices generally represent stakeholder’s endpoints and expose interfaces to automated operations. Current trends in communication allow more applications and devices to perform functions traditionally allocated to the transportation ITS infrastructure. This connected environment of industrial internet of things presents design challenges because of the diversity of stakeholders, interfaces, and the messages among them. This may require new ways in which ITS planning can handle the scale and complexity of these highly connected systems. This work focuses on the modeling of the architecture of a freight-focused ITS application, including maritime ports. The proposed model integrates stakeholders, behaviors, and messages using the Systems Modeling Language (SysML). The key contribution of this work is to demonstrate the creation of an executable SysML model for an ITS application without sacrificing the typical Systems Engineering Management Plan artifacts (e.g., requirements traceability matrices and interface control documents). At the same time, the proposed model provides a re-usable pattern to support parametric analysis of candidate architectures with respect to any measure of effectiveness. This allows establishing a single source of architecture definition and having multiple architecture specializations depending on the measure of effectiveness being evaluated. Recommendations for implementation and integration with existing ITS tools are provided.