The Australian Capital Territory (ACT) has the highest cycling participation rate in Australia; however it also has one of the highest rates of cyclist serious injury. In this study, the behaviour of cyclists and their interaction with drivers was investigated to identify ways to improve cyclist safety. A naturalistic cycling study was conducted using helmet mounted video cameras with a GPS data logger. The study included an online survey and in-depth exit interviews. In total, 36 participants completed the study from September 2011 to April 2012. Participants recorded over 460 hours of video footage of their commute to and from work over a distance of almost 9,000km. In total, 91 potential conflict events were identified that involved the cyclist and another road user. The majority of the events involved the cyclist and a driver and were due to actions by the driver. Drivers turning left across the cyclist’s path and unexpectedly opened vehicle doors were the most common interactions. Cyclists recorded an average speed of 22.7km/h and a maximum speed of 56km/h. Data on cyclists’ speed provides new insights into how cyclists travel, particularly on-road and when interacting with other road users. Potential countermeasures and recommendations to improve safety for cyclists in the ACT are also discussed.