Fatalities and head injuries from bicycle-related crashes remain a concern in the United States. Despite legislation in many states, helmet use remains low. This observational study examined the helmet use and related factors in a North Carolina city. The sample consisted of 2088 observations of bicyclists. The objectives were to (1) determine helmet use; (2) describe other safe bicycling practices; and (3) examine the relationship of demographic variables and safe riding practices with helmet use. Helmet use was observed for 25% of the sample. Demographic factors related to helmet use were being female (OR = 1.32), 26 years old or older (OR = 4.94), and White (OR = 2.17). Bicyclists riding on the road with traffic were more likely to wear a helmet than bicyclists riding on the sidewalk (OR = 2.04). Findings indicate that helmet use remains low in the city. Research to monitor, better understand, and promote helmet use is needed.