Introduction: We seek to characterize unhelmeted injured cyclists presenting to the emergency department (ED): demographics, cycling behaviour, and attitudes towards helmet use. Methods: This was a prospective cohort study in a downtown teaching hospital, from May 2016 - Sept 2019. Injured cyclists presenting to the ED were recruited if they were not wearing a helmet at time of injury and over age 18. Exclusion criteria included intoxication, inability to consent, or admission to hospital. A standardized survey was administered by a research coordinator. Descriptive statistics were used to summarize the data, and survey responses reported as percentages. Results: We surveyed a convenience sample of 68 unhelmeted injured cyclists (UICs) with mean age of 33.6 years (range 18 to 68, median 29.5 years). Ratio of males to females was 1:1. The majority of UICs cycled most days per week or every day in non-winter months (89.6 %, n = 60). Cycling in Toronto was perceived as somewhat dangerous (45.6%, n = 31) or very dangerous (5.9%, n = 4) by most, and very safe (2.94 %, n = 2) or somewhat safe (19.12%, n = 13) by few. Almost a third (29.4 %, n = 20) had been in a cycling accident in the prior year, some of these (15.0%, n = 3) prompting an ED visit. All cyclists were riding their personal bike (100 %, n = 68) at time of injury, and most (98.5%, n = 67) had planned to cycle when they departed home that day. Purpose of trip was primarily for commuting to work (50%, n = 34), social activities (19.1%, n = 13), school (7.4%, n = 5), and recreation (7.4%, n = 5). Bicycle helmet ownership was low (41.2 %, n = 28). UICs reported rarely (10.3%, n = 7) or never (64.7%, n = 44) wearing a helmet when cycling. Reported factors discouraging helmet use included inconvenience (33.8%, n = 23), lack of ownership (32.4%, n = 22), discomfort (29.4%, n = 20), and ‘messed hair’ (14.7%, n = 10). Few characterized helmets as unnecessary (10.3%, n = 7) or ineffective (1.5%, n = 1). The majority had a college diploma or more advanced education (77.9%, n = 53), and spoke English at home (85.3%, n = 58). Conclusion: Unhelmeted injured cyclists surveyed were frequent commuter cyclists who do not regard cycling as safe, yet choose not to wear helmets for reasons largely related to convenience rather than perceptions regarding safety or necessity. Initiatives to increase helmet use in this subgroup should address the reasons given for not wearing a helmet, potentially using principles of adult education and behavioral economics.