By revisiting its history from 1870 down to the present, this essay examines the role played by the figure of the parkway – both as idea and as object – in the urban development of the New York metropolitan area. It is the ‘Odyssey’ that interests us here: from the emergence of the Brooklyn parkways designed by Frederick Law Olmsted and Calvert Vaux, to the invention as a total project of the first modern parkway along the Bronx river, from the deployment of a system of regional parkways planned by Robert Moses in the 1930s to its obliteration in the face of the prominent development of highways, followed by the first attempts to rehabilitate historic parkways in the 1970s, when the city was going through a major crisis. Today, the renewed interest of designers and historians has made the parkway an important part of the heritage of urban planning, confronted with major projects and operations that mobilize different scales, uses and disciplines, between conflicting urban policies and temporal shifts. By looking back on its past and projecting its future, the inventory of the New York Parkway history provides valuable lessons with regard to the global changes affecting the contemporary city.