This paper investigates the evolution of urban cycling in Montreal, Canada and its link to both built environment indicators and bicycle infrastructure accessibility. The effect of new cycling infrastructure on transport-related greenhouse gas (GHG) emissions is then explored. More specifically, we aim at investigating how commuting cycling modal share has evolved across neighborhood built-environment typologies and over time in Montreal, Canada. For this purpose, automobile and bicycle trip information from origin–destination surveys for the years 1998, 2003 and 2008 are used. Neighborhood typologies are generated from different built environment indicators (population and employment density, land use diversity, etc.). Furthermore, to represent the commuter mode choice (bicycle vs automobile), a standard binary logit and simultaneous equation modeling approach are adopted to represent the mode choice and the household location. Among other things, we observe an important increase in the likelihood to cycle across built environment types and over time in the study region. In particular, urban and urban-suburb neighborhoods have experienced an important growth over the 10 years, going from a modal split of 2.8–5.3% and 1.4–3.0%, respectively. After controlling for other factors, the model regression analysis also confirms the important increase across years as well as the significant differences of bicycle ridership across neighborhoods. A statistically significant association is also found between the index of bicycle infrastructure accessibility and bike mode choice – an increase of 10% in the accessibility index results in a 3.7% increase in the ridership. Based on the estimated models and in combination with a GHG inventory at the trip level, the potential impact of planned cycling infrastructure is explored using a basic scenario. A reduction of close to 2% in GHG emissions is observed for an increase of 7% in the length of the bicycle network. Results show the important benefits of bicycle infrastructure to reduce commuting automobile usage and GHG emissions.