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After 1900, the coming of the automobile set in motion a series of events that transformed the physical structure, population distribution, and transportation patterns of the modern American city. In the early auto era, some landscape architects and city planners promoted parklike motorways, such as New York's Bronx River Parkway, completed in 1923, and the Long Island parkways built by Robert Moses in the 1920s. These winding, landscaped parkways served wealthy suburban commuters and offered pleasant auto excursions for Sunday drivers, but they did not provide a useful traffic model for modernizing cities. By 1930, more than 26 million cars and trucks crowded American streets and roads. Motorists and their political allies battled with pedestrians and streetcar companies for control of the streets. Street widenings and uniform traffic regulations did little to ease the daily crush of cars heading to central business districts. In the 1920s, political and business leaders in a few cities responded to traffic congestion by supporting construction of elevated, limited-access express highways, such as New York's West Side Elevated Highway and Chicago's Wacker Drive, while Detroit began planning 300 miles of radial “superhighways” that eliminated grade crossings.

In the 1930s, rising automobile usage, relentless urban traffic congestion, and a corresponding decline of urban transit fostered new forms of urban planning to accommodate Americans' preference for private automobile travel. In February 1930, American City magazine announced the arrival of “The Freeway—A New Kind of Thoroughfare,” and the term freeway caught on. The automobile industry, eyeing the huge urban market for cars, promoted the necessity for such express highways in the 1930s and after. General Motors' Futurama exhibit at the New York World's Fair of 1939 stimulated such thinking. In his Futurama exhibit and in a subsequent book, Magic Motorways (1940), industrial designer Norman Bel Geddes provided a glimpse of the “cities of tomorrow,” with elevated freeways speeding traffic through great skyscraper cities at speeds up to 100 miles per hour. About the same time, engineers in the Bureau of Public Roads (BPR), the federal agency that cooperated with states on road-building projects, issued its report, Toll Roads and Free Roads (1939). Authors of the BPR report emphasized the need for high-speed, limited-access highways linking the major cities of the nation. BPR engineers also recommended an urban component to the system: expressways that would both penetrate and encircle the central cities, along with radial links that tied the urban highway network together. Embraced by President Franklin D. Roosevelt, the BPR report provided the foundation for the present interstate highway system. The completion in 1940 of the Pennsylvania Turnpike and the first segment of the Hollywood Freeway in Los Angeles offered a peek at the nation's highway future. Both roads were substantially financed through New Deal public works programs.

Between 1942 and 1946, wartime financial restraints postponed road building. The BPR issued a second report in 1944, Interregional Highways, mapping a 39,000-mile interstate system, but leaving the urban freeway segments for subsequent planning. The Federal-Aid Highway Act of 1944 incorporated much of the BPR's report, but funding remained inconsequential. Meanwhile, big-city mayors, city managers, city planners, and downtown commercial, financial, and real estate interests lined up in support of a major postwar reconstruction of urban America. They all conceived of inner city expressways as essential to the rejuvenation of the central business districts already threatened by population dispersion and economic decentralization. During the decade after 1945, the federal government appropriated matching 50/50 funds to the states to support highway building, but limited funding and squabbling between rural and urban interests frustrated freeway advocates. By the early 1950s, leaders in many cities, including San Francisco, Los Angeles, Seattle, Houston, Dallas, Denver, Chicago, Detroit, Cleveland, Pittsburgh, New York, Miami, and Jacksonville, began planning and building their own freeway systems. Several states, including Florida, New York, New Jersey, Ohio, Indiana, Connecticut, and Massachusetts, began building long-distance, limited-access toll highways, such as the Florida Turnpike, the Indiana Toll Road, and the New York State Thruway.

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