This study investigated the associations of youth cigarette smoking with tobacco outlet densities and proximity of tobacco outlets to youth homes and schools across different buffers in 45 midsized California communities. The sample comprised 832 youths who were surveyed about their smoking behaviors. Inclusion criteria included both home and school addresses within city boundaries. Observations in the 45 cities were conducted to document addresses of tobacco outlets. City- and buffer-level demographics were obtained and negative binomial regression analyses with cluster robust standard errors were conducted. All models were adjusted for youth gender, age, and race. Greater densities of tobacco outlets within both a 0.75 and 1-mile buffer of youth homes were associated with higher smoking frequency. Neither tobacco outlet densities around schools nor distance to the nearest tobacco outlet from home or school were associated with youths past-30-day smoking frequency. Lower population density and percent of African Americans in areas around homes and lower percent of unemployed in areas around schools were associated with greater smoking frequency. Results of this study suggest that restricting outlet density within at least 1-mile surrounding residential areas will help to reduce youth smoking.