A New England city composed of rich history, a strong cultural identity, and diverse groups of people; Portland, Maine is acknowledged as a city for the people. The wharves along the harbor’s edge of the city create an important symbolic reminder within the city of the centuries of fishing and trading that supported the state of Maine. As the population of the city grew over time, the wharves became disconnected with the expansion of vehicular infrastructure. This thesis explores the cultural identity of Portland’s waterfront edge and the possibility of reconnecting the flourishing waterfront industries with the urban fabric through sustainability, master planning techniques and technological advancements that will address current environmental issues. This thesis further explores the pedestrian experience in the city by proposing an architecture that will enhance these experiences through stronger connections with local culture and communities.