Background: Musculoskeletal disorders consequent to demanding working conditions are not uncommon nowadays. A number of risk factors contribute to these problems thereby affecting occupational productivity. Most commonly affected are the transport sector workers, who are subjected to harsh conditions of the environment, traffic noise, pollution, difficult shifts, lack of sleep, prolonged abnormal posture, and so on. This study was undertaken to assess the social and work factors of transport sector workers, mainly drivers and conductors, in Dakshina Kannada district and to make an association between these and the morbidity status of the individuals. Objectives: The study was undertaken to assess the type and degree of work-related musculoskeletal disorders in transport sector workers. The effect of duration in the occupation on co-morbidities present among these drivers and conductors was also analyzed. The study was also aimed at evaluating ocular symptoms in these workers. Materials and Methods: The present study was a cross-sectional, community-based descriptive study. A total of 522 transport sector workers were included as part of the study. A prestructured, pretested, and validated questionnaire for sociodemographic details and occupational-related morbidity were used for data collection. Results: All study subjects were male and in the age range of 21–55 years. The stressors responsible for morbidities were identified. A positive correlation was found between long working hours and ill-health. Drivers were found to have additional issues in terms of ocular symptoms. Individuals working for more than 5 years in the transport sector were found to have the most number of medical complaints. Conclusion: Long working hours, postural strain, and exposure to noise, environmental pollution, sunlight, and dust are all factors contributing to transport sector morbidities. Drivers were found to face the maximum brunt of all these factors compared to conductors. Mental strain and stress were found to be present in all of these individuals.