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Recently, researchers have proposed to develop automated self-balancing functions for bicycles to increase road safety and convenience. However, no study has investigated how self-balancing bicycles are perceived by potential users in a natural urban environment. Therefore, we conducted a field study using a modified “parent-child tandem” in which both the front and back seat passengers could share control of the riding dynamics. An experimenter in the back seat acted as an automated system, and participants in the front seat experienced the ride while responding to text messages on their smartphones. Based on interviews, video observation, and eye-tracking data, the results highlight potential use cases for self-balancing bicycles and uncover that trust and multitasking freedom can lead to similar problems as in automated cars.