Bicycling for transportation is experiencing a resurgence in much of the U.S. Consequently, the question of facility design has become a hot research topic. However, most such research is conducted in areas with strong bicycling cultures, which misses a critical link of how facility design can help shape bicycling culture. This dissertation contains analyses on data from a dual-wave survey deployed between 2016 and 2018 in communities in the Southern United States. To varying degrees, these are communities where cycling is not (yet) popular and/or widely adopted, a setting that is much more representative of the nation at large. The first analysis is on a subset of the data from the first-wave survey (N=1,178), in which quantitative analyses including linear regression models are used to estimate perceived comfort, perceived safety, and willingness to try bicycling facilities. Facilities that limited interaction with automobile through, turning, and parking traffic were found to be perceived as more desirable among cyclists. The second analysis contains the full first-wave sample (N=2,157) including respondents in neighborhoods in Atlanta, GA. Latent class models were estimated with attitudinal factors such as bicycle enjoyment and risk tolerance as class membership covariates, with results indicating the presence of a latent class of pro-bicycling but risk-cautious respondents whose perceptions differ from those of their pro-bicycling, risk-embracing counterparts by the relatively greater impact of protected bicycle facilities.