The built environment, cyclist behavior, and driver interactions can influence route choice and, ultimately, cyclist safety. Recent studies use crowdsourced data, such as Strava, to document route selection; however, aggregated data may not fully explain the factors underpinning route selection. Utilizing naturalistic methods, we analyze videos of recorded rides and GPS data from six cyclists ... [Show full abstract] representing three types of riders-commuters, recreational, and athletes-to explore route choices, behavior, and driver interactions in Tucson, Arizona. Our analysis of three route selection cases highlights how intersection design, driver interactions, pavement conditions, and type of riding lead cyclists to modify behaviors and select longer detours to avoid unsafe intersections. Additionally, our study combines Strava heatmaps and physical bicycle counts to explore the number of cyclists potentially facing similar factors influencing route choice. By studying cyclists with different riding aims and utilizing both Strava heatmaps and video recordings, researchers can determine the underlying conditions, identify route locations in need of improvements, and collaborate with practitioners to implement changes to increase cyclist safety through appropriate solutions. This analysis can help ensure that designs meet user expectations.