Owing to its beneficial effects, many governments encourage bicycle use for commuting. In search of effective strategies, they often study best practices from elsewhere. However, in order to assess the likely success of transferring measures from one city or country to another, an accurate comparison of the bicycling context is needed. This article explores the similarities and differences in attitudes and beliefs about the decision to commute by bicycle to work in two bicycling-oriented cities: Delft, the Netherlands, and Davis, California, in the U.S. Because bicycling conditions are good in both cities, it is possible to explore the role that attitudes play in the decision to cycle to work. Analyses indicate that beliefs about safety and the importance attached to environmental benefits differ between the cities. Social norms about cycling are important in both cities, but residents in Davis are more often confronted with negative reactions to cycling. Similarities are found in beliefs towards the health benefits of cycling. Strategies successful in one city in encouraging cycling by targeting or leveraging health therefore offer promise for the other city. This exploration provides an important starting point for large-sample comparative studies of attitudes towards bicycle commuting.