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In the second half of the twentieth century, America's cities and suburbs were engulfed by suburban sprawl - the movement of people (especially middle-class families) and jobs from older urban cores to newer, less densely populated, more automobile-dependent communities generally referred to as suburbs. Cities throughout America lost population to their outlying suburbs, and cities that gained population usually did so only because they were able to annex those suburbs. America's suburban revolution has not left Jewish communities unscathed. For example, the city of Newark, New Jersey, contained 58,000 Jews and thirty-four synagogues in the 1940s, but today has only a few hundred Jews and only two synagogues. Similarly, the city of St. Louis, Missouri, now has only one synagogue, although its suburbs have over twenty. Even in more vibrant cities, significant Jewish flight has occurred. In 1990, two-thirds of metropolitan Chicago's Jews lived in suburbs, up from 4% in 1950. This flight to suburbia has affected Jews' daily lives dramatically. Suburban Jews, like other American suburbanites, are highly dependent on automobiles. This article discusses the tension between suburban sprawl and Jewish values. Specifically, the article argues that the automobile dependency and class division exacerbated by sprawl conflict with Jewish ethical and environmental values and impede observance of Jewish law. In addition, the article rebuts libertarian objections to anti-sprawl policies by pointing out that Jewish law encourages public regulation of land use, and that in any event, anti-sprawl policies need not conflict with libertarian norms.