Women are less likely to ride than men in low cycling countries such as Australia. In Australia, self-reported cycling participation appears to be declining, particularly for women. This paper examines the rider and road environment correlates of women’s cycling. While most earlier studies relied on self-report data to understand gender differences in cycling, this study video-recorded 24,868 riders (22 % female) at 17 sites across Queensland, Australia. The probabilities of an observed rider being female under different circumstances (e.g., speed limit, riding location, time of riding, group riding) at these sites were modelled in a binomial logistic regression framework. The likelihood of a rider being a woman was greater during the day (9am-8pm) than the early morning (5–9 a.m.); on weekends than on weekdays; in groups of two or more riders than among single riders; in lower speed zones than speed zones of 60 km/h or over; on roads with bike lanes or multiple traffic lanes or raised medians than on roads without these, and in urban areas than suburban areas. The likelihood of the rider being a woman was lower among those riding road bikes than other types of bicycles. The use of a naturalistic study design marks the key strength of this paper. Findings of this study should help better understand women’s cycling patterns and preferred cycling locations, which cycling communities and organisations can use to advocate for better roads and paths that make female riders feel safe.