With the increase in the number of cyclists, a method to evaluate the satisfaction of cyclists has become necessary. Previous studies in Europe and America have reported several approaches to evaluate cyclists’ perception of satisfaction. This research explored an emerging technology using 360° videos to develop a method for investigating cyclists’ level of satisfaction on both sidewalks and paved shoulders in Japan. The 360° videos provide a high level of immersion compared with traditional videos. All 360° videos were filmed at sixteen different locations in Kumamoto city, Kyushu island. Participants were asked to take a video survey by viewing the 360° videos with a head-mounted display and then rating their level of satisfaction. Finally, based on the results of the video survey, both multinomial ordered logit regression model and random parameters multinomial ordered logit regression model were used to explain the relationships between cyclists’ satisfaction, traffic conditions, and road characteristics. The results show that the road characteristics variables for both sidewalks and paved shoulders have statistically significant effects on participants’ satisfaction (p < 0.05). On the other hand, traffic conditions variables did not have an impact on participants for sidewalks section. In particular, there is data available on all the variables in the model that allows planners and engineers use this method to evaluate the satisfaction of cyclists on various road segments.