Greenways provide multiple benefits for trail users’ individual experiences based on users’ background environment and their perceptions of characteristics such as the trail width, vegetation, water, and facilities. Although greenway trail characteristics are important factors that affect users’ preferences, only a few studies have examined individuals’ experiences of greenways based on their perceptions and preferences. The purpose of this study is to examine how greenway trails can be designed to improve users’ experiences in relation to their perceptions and preferences by considering trail characteristics. We examine the relationship between greenway trail characteristics and likability using t-tests as well as correlation and multiple regression analyses. In the current study, virtual tour surveys of greenway users were conducted, with two urban greenway trails as the study sites: Town Lake Trail in Austin, Texas, and Buffalo Bayou Trail in Houston, Texas. Perceptions of all eight greenway trail characteristics, except for background buildings, were significantly different between the trails, and a significant difference in likability was found for five characteristics (the presence of water, trail facilities, trail width, adjacent automobile traffic, and built structures on the trail). In addition, the results of the correlation and multiple regression analyses revealed that the presence of water, amount of vegetation, automobile traffic, and built structures were correlated with likability. These findings suggest that designing appropriate types of greenway trails can help increase users’ likeability ratings of urban greenways. This study contributes to the enhancement of trail environments by providing strategies for practitioners to effectively design and manage greenways.