Although transportation’s impacts on physical health are relatively well-established, the relationship between transportation and subjective well-being (SWB) has been the subject of recent focus. Policymakers attempt to improve the health and well-being of populations through interventions to improve transportation experiences and promote sustainable transport modes, while researchers studying these connections seek valid and reliable measures of SWB in the travel domain. Studies consistently find travel by walking and bicycling to be rated more positively than automobile travel, yet many use single measures of travel SWB, obscuring nuanced variations between modes.Using the results of a Portland, Oregon, survey of nearly 700 commuters, this study investigates modal differences and other potential determinants of detailed, multidimensional measures of travel SWB. Specifically, the Satisfaction with Travel Scale as well as new measurement models of travel affect (distress, fear, attentiveness, and enjoyment) and travel eudaimonia (security, autonomy, confidence, and health) are examined for variations between modes. Structural equation models predicting the latent variable constructs as a function of trip and traveler characteristics yield valuable behavioral and psychological insights. Walking and bicycling rated much higher on measures of physical and mental health, confidence, positive affect, and overall hedonic well-being, suggesting significant benefits of physically active commutes. However, cycling commuters scored higher on distress and fear and lower on security, highlighting the value of multidimensional measures of travel SWB. Enhancing the quality of the traveling experience by various modes—such as making bicycling feel safer through protected infrastructure—could significantly improve commuters’ well-being.