As the consequences of automobile dependency have become increasingly apparent, national discourse has shifted toward rebuilding America’s once-famed passenger rail infrastructure and creating a national network of high-speed rail lines as well as improvements to existing commuter and regional rail services. In order for New York to retain its role as a leader in the global economy and harness the potential of high-speed rail, it must create a viable facility to serve as a gateway to the city and as a hub for multiple modes of transit. New York Penn Station, as it stands today, is woefully inadequate for that purpose. This thesis project examines the possibility of creating a new and expanded Penn Station as a gateway to New York, while improving its connections to other transit modes and the surrounding context. The project proposes expanding the station structure one block to the south, and replacing its labyrinthine network of confusing passageways with an open, light-filled structure with simplified circulation patterns that provide for an appropriate sense of arrival in New York. The outcomes of the research include historical research and an examination of the facility’s present-day uses in the form of a written document, as well as precedent research on other facilities that have undergone similar transformations. The design proposal consists of diagrams, drawings, and renderings. Together, these demonstrate the viability and potential rewards of rebuilding Penn Station as a gateway to the city and a hub of activity in West Midtown.