Since 1973, New York City's Route 9A from Battery Park to West 59th Street has undergone a transformation from a crumbling 1930s elevated highway in a derelict postmaritime environment of rotting piers and abandoned buildings to a first-class multimodal, at-grade, tree-lined urban boulevard with a recreational focus. Route 9A connects Lower Manhattan and the west side of Manhattan with Hudson River Park and the waterfront and is a premier example of the economic revitalization that can take place when urban design and community involvement combine with engineering and the environment. The New York State Department of Transportation reconstructed Route 9A in seven segments, bid as seven contracts. As the last contract adjacent to the World Trade Center was winding down, the terrorist events of September 11, 2001 (9/11), occurred. With the devastation came the rebuilding of Lower Manhattan and a new emphasis on people, environment, and coordination in a post-9/11 environment. Route 9A was and continues to be a vital link. This paper describes the process of transformation and how adversity experienced along the way was overcome—beyond Westway and post-9/11 at the World Trade Center—as well as the citizens’ vital role in rebuilding Route 9A.