Master of Regional and Community Planning / Department of Landscape Architecture/Regional and Community Planning / John W. Keller / The purpose of this report is to identify the role of transportation linkages in facilitating economic development in Portland, Maine, and the surrounding region, beginning with the city’s 19th century maritime economy. In the process, this study demonstrates how the evolution of Portland’s economy, from early mercantile capitalism, through the industrial and post-industrial eras, was greatly shaped by a succession of transportation developments, engineered by city leaders. Research reveals that these achievements were coordinated through both public sector planning and private sector entrepreneurship, to cultivate comparative advantages for the city. Evidence of this implicit collaboration is apparent in the growth of new economic sectors to support local shipping, rail, freight, and eventually commercial airline service. As a result of these efforts, Portland maintains a status as a regional economic gateway that is disproportionate to its modest population of fewer than 70,000 residents. In support of this argument, this report will also present relevant historical anecdotes to provide context for the growth of the city and broader region as a whole, from colonization through globalization. As part of the city’s economic history, this discussion demands an examination of the macroeconomic forces that contributed to the rise and fall of the local maritime industries, manufacturing, and the 21st century service sector economy. Additionally, this report will discuss the impact of major global events, including war, recession, and the telecommunication revolution, all of which have precipitated major socio-economic changes across the United States. The report concludes by offering insight into Portland’s future, with specific respect to the 2008 economic crisis and the resulting impact on the local real estate and financial markets. Despite an economic climate that threatens the viability of small cities across the United States, Portland’s history of resilience provides hope for a prosperous future. In light of the city’s modern economic trajectory, the ability to a chart a new course will rely upon progressive leadership that can capitalize on the region’s natural geographic resources. These future developments will, no doubt, parallel a new wave of investment in local infrastructure and transportation linkages.