This paper analyzes the relationship between network supply and travel demand and describes a road development and degeneration mechanism microscopically at the link (road-segment) level. A simulation model of transportation network dynamics is developed, involving iterative evolution of travel demand patterns, network revenue policies, cost estimation, and investment rules. The model is applied to a real-world congesting network for Minneapolis-St. Paul, Minnesota (Twin Cities), which comprises nearly 8000 nodes and more than 20,000 links, using network data collected since 1978. Four experiments are carried out with different initial conditions and constraints, the results of which allow us to explore model properties such as computational feasibility, qualitative implications, potential calibration procedures, and predictive value. The hypothesis that road hierarchy is an emergent property of transportation networks is corroborated and the underlying reasons discovered. Spatial distribution of capacity, traffic flow, and congestion in the transportation network is tracked over time. Potential improvements to the model, in particular, and future research directions in transportation network dynamics, in general, are also discussed.