In what is one of the first visual preference surveys using Google Street View through a free tool StreetSeen (http://streetseen.osu.edu), adult students viewed a series of paired slides of image of city streets. Participants were asked to choose which image from the pair they preferred based on which street they would prefer to ride a bicycle. Subsequent analyses showed that differences in continent of the respondent impact preferences. This research demonstrates the extent to which certain segment-level factors such as presence of trees along the street, width of the street, presence of sidewalks, and other features are preferred using discrete choice models. The models reveal that increasing vehicle traffic, number of lanes, streetscapes with dense trees, and presence of parking lots decrease the probability of being chosen. Having sidewalks, presence of pedestrians, trees set back from the street, and traffic calming devices are positively associated with respondents’ preferences. The results related to trees may relate to perceptions of safety. For example, dense trees close to a street may limit visibility along a roadway. The models also reveal significant differences in preferences based on respondents’ locations. We conclude that this method is effective in capturing information about bicycling preferences. The survey methodology and analysis techniques introduced in this study can help city planners design streets that are preferred by bicyclists.