Introduction: We aimed to describe the prevalence, in-store location, and neighborhood predictors of point-of-sale smokeless tobacco advertising. Methods: In 2007, we conducted assessments of smokeless tobacco advertising at the point of sale in 484 establishments, which held tobacco licenses and sold tobacco products in a Midwest metropolitan area. Associations between store characteristics, neighborhood characteristics (based on U.S. 2000 census block groups), and smokeless tobacco advertising were calculated. Results: Advertisements for smokeless tobacco were found in 21% (n = 103) of stores. Approximately, 12% (n = 58) of stores had ads within 6 feet of the counter, 3% (n = 14) had ads less than 3 feet from the ground, and 2% (n = 9) had advertisement less than 1 foot from candy or snacks. The racial/ethnic composition and number of households on public assistance within the block group in which a store was situated were related to the amount of smokeless advertising in stores. For instance, having a higher proportion of the population identifying as White was associated with more advertising. Gas stations/convenience stores had more advertising than any other store types. Chain stores had double the amount of advertising as independent stores (p < .05) even after adjustment for other factors. Conclusions: Smokeless tobacco advertising is not uncommon even in an urban metropolitan community. These products are being advertised in a way that youth, especially those living in neighborhoods with certain demographic characteristics, can encounter. With Food and Drug Administration regulation, there are new opportunities to regulate advertising at the point of sale.