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Abstract: We present theory and evidence highlighting the disamenity effects of freeways on neighborhoods and the spatial structure of cities. In our model, disamenity effects–e.g., from land use exclusion, negative externalities, or barriers between neighborhoods–dominate access benefits in downtown neighborhoods compared with outlying areas, where access benefits are greater. These margins are especially relevant for understanding the nationwide freeway revolts that spread after 1955, setting central-city residents concerned about quality of life against regional planners who saw expanding transportation networks as key to urban growth. We confirm several predictions of the model using panel data on population, income, employment, and travel behavior in U.S. cities and neighborhoods between 1950 and 2010. To address the endogenous allocation of highways to cities and neighborhoods, we use planned-route and historical-route instrumental variables. We also show evidence that actual freeway construction diverged from initial plans in the wake of the growing freeway revolt and subsequent policy responses. Over the 1960s, freeway construction increasingly took place in neighborhoods that were initially less educated and more black. Finally, we use a calibrated city structure model to quantify the effects of freeways, via amenity and transportation cost channels, on both central neighborhoods and citywide outcomes.