Many healthcare workers are “on the road” traveling to and from fixed sites (eg, patients’/clients’ homes). Qualitative interviews with nine Nova Scotian managers of mobile healthcare workers explored the conditions of workers’ travel. Findings highlight challenges such as changing schedules, as well as positive features including flexibility over the travel schedule. Some managers noted worker mobility-related responsibilities including having to decide if travel is too dangerous due to poor weather. A few managers suggested that workers may not receive adequate economic reimbursement for travel costs (eg, wear and tear on vehicle), and in some instances, workers need to use a benefit (eg, vacation day) or are not paid if they cannot drive due to poor weather. Reported organizational supports for workers’ travel were variable. This research indicates a need for supportive mobility-related policies and practices across all organizations, including policies that cover economic costs related to travel for all workers.