This study aimed to build on past findings about differences in personal walking experiences by demonstrating what elements were beneficial to participants with different walking habits. Accordingly, this study established the relationships between valued walking elements and people’s motivation to walk, by dividing participants into three groups: Group W for people with a walking habit, Group HW for people who walk occasionally but not regularly, and Group NW for people who do not walk habitually. Participants walked a familiar and an unfamiliar route with a wearable device that recorded their heart-rate variability and electrodermal activity. Changes in the biometric data helped to identify the defining moments in each participant’s walk. Participants discussed these moments in one-on-one interviews with a researcher to pinpoint their valued walking elements. As a result, this study classified walking elements into six themes: “Surroundings,” “Social,” “Exploration,” “Route Plan,” “Physical Exercise,” and “Mental Thinking.” A walking habit development model was made to show how “Route Plan” and “Exploration” were beneficial to Group NW, “Social” and “Surroundings” were beneficial to Group HW, and “Route Plan,” “Mental Thinking,” and “Physical Exercise” were beneficial to Group W.