This research presents a regional analysis of cycling behaviour, relating to both work and nonwork trips, in the Greater Toronto and Hamilton Area (GTHA), Canada. A set of negative binomial regressions were estimated using travel data from the 2011 Transportation Tomorrow Survey, which identified several socio-demographic, built environment and trip characteristics correlated with cycling rates. In general, the results indicated that the neighbourhood environment and travel distance had more important influences on work trips in comparison to non-work trips. Additionally, the model outcomes were mapped, a process that helped identify local differences in the propensity of cycling across the GTHA region. This study proposes an easy-to-implement analytical framework to enable examination of cycling behaviour and identification of cycle-friendly communities, at a regional scale, and perhaps systematically direct limited resources available to improve cycling rates by targeted localities across a metropolitan region with suitable socio-demographic and built environment characteristics.