Exposure to retail tobacco marketing is associated with youth smoking, but most studies have relied on self-reported measures of exposure, which are prone to recall bias. To examine whether exposure to retail cigarette advertising, promotions, and retailer compliance is associated with youth smoking-related outcomes using observational estimates of exposure. Data on retail cigarette advertising and promotions were collected from a representative sample of licensed tobacco retailers in New York annually since 2004. County-level estimates of retail cigarette advertising and promotions and retailer compliance with youth access laws were calculated and linked to the New York Youth Tobacco Survey, administered to 54,671 middle and high school students in 2004, 2006, and 2008. Regression models examined whether cigarette advertising, promotions, and retailer compliance were associated with youth's awareness of retail cigarette advertising, attitudes about smoking, susceptibility to smoking, cigarette purchasing behaviors, and smoking behaviors. Living in counties with more retail cigarette advertisements is associated with youth having positive attitudes about smoking (odds ratio [OR] = 1.10, 95% confidence interval [CI] = 1.03-1.19, P < .01). Living in counties with more retail cigarette promotions is associated with youth current smoking (OR = 1.57, 95% CI = 1.01-2.44, P < .05). Living in counties with higher retailer compliance with youth access laws is associated with higher odds of youth being refused cigarettes when attempting to buy in stores (OR = 1.12, 95% CI = 1.01-1.25, P < .05) and lower odds of retail stores being youth's usual source of cigarettes (OR = 0.88, 95% CI = 0.80-0.97, P < .01). Strong retailer compliance programs and policies that eliminate cigarette advertising and promotions may help reduce youth smoking.