While the industry of civilian unmanned aerial vehicles (UAV) or drones has seen rapid expansion in the past decade, few studies have systematically examined the dynamics between this disruptive technology and various aspects of cities. Employing quantitative methods, this dissertation explores 1) the diffusion and adoption patterns of civilian drones; 2) how cities manage the challenges of increasing drone activities; and 3) the supply-side opportunities and constraints associated with the deployment of Urban Air Mobility (UAM) in built-out metropolitan areas. The results of the first county level study might suggest (Chapter 2) that the digital divide has magnified the uneven and nonlinear diffusion of drones across time and space. Furthermore, the strength of state-level interventions correlates with the intensity of local drone adoption, even though the regulatory effects are different among drone user groups. People living in neighborhoods with a higher adoption rate of drones are on average younger, more affluent, and Whiter. An extension of the first study at the zip code level (Chapter 3) has retested the key results and provided additional insights into the spatial dependence effects that affect the drone adoption patterns. Furthermore, the results of the second study (Chapter 4) indicate that local drone policy adoption among communities of color trails behind that of other communities. Although drone policy adoption at the local level has been shaped by both motivation and capacity factors, the desire to protect public facilities appears to motivate localities to adopt regulatory measures. In particular, policy adoption is influenced by what nearby cities do, suggesting that strategic interaction is at play among local governments. In the third study (Chapter 5), I evaluate the supply-side opportunities and constraints associated with UAM adoption through a systematic scenario analysis. The results of the third study indicate that current supply-side infrastructure opportunities in Southern California, like helipads and elevated parking structures, are widely available to accommodate the regional deployment of UAM service although current spatial constraints can significantly limit the location choice of UAM landing sites (vertiports) for electric vertical take-off and landing (eVTOL) aircraft. Moreover, the low-income and young populations tend to live relatively farther away from the supply-side opportunities compared to the general population. The third study also proposes a network of UAM stations in Southern California based on the joint considerations of available infrastructure and home-workplace commuting flows.