This study was designed to estimate the relationship between exposure to tobacco retail outlets and smoking initiation in a racially diverse urban setting. Using data from the 2011 NYC Youth Risk Behavior Survey, multivariable logistic regression analyses were conducted to estimate the exposure-initiation relationship and test for effect modification, while controlling for covariates. The predicted probability of smoking initiation from the multivariable model increased from 7.7 % for zero times a week exposed to tobacco retailers to 16.0 % for exposure seven times or more per week. The odds of initiation were significantly higher among adolescents exposed to tobacco retail outlets two times or more a week compared with those exposed less often (AOR = 1.41; 95 % CI: 1.08, 1.84). Risk-taking behavior modified the relationship between exposure and initiation, with the odds of initiation highest among those low in risk-taking (AOR = 1.78; 95 % CI: 1.14, 1.56). These results are consistent with past research, showing that frequent exposure to tobacco marketing in retail settings is associated with increased odds of initiation. Reducing exposure to tobacco retail marketing could play an important role in curtailing smoking among adolescents, especially those less prone to risk-taking.