Increased logging mechanization has helped improve logging safety and health, yet related safety risks and concerns are not well understood. A cross-sectional study was completed among Virginia loggers. Participants n = 122) completed a self-administered questionnaire focusing on aspects of safety and health related to logging equipment. Respondents were at a high risk of workplace injuries, with reported career and 12-month injury prevalences of 51% and 14%, respectively. Further, nearly all (98%) respondents reported experiencing musculoskeletal symptoms. Over half (57.4%) of respondents reported symptoms related to diesel exhaust exposure in their career. Few (15.6%), however, perceived their jobs to be dangerous. Based on the opinions and suggestions of respondents, three priority areas were identified for interventions: struck-by/against hazards, situational awareness (SA) during logging operations, and visibility hazards. To address these hazards, and to have a broader and more substantial positive impact on safety and health, we discuss the need for proactive approaches such as incorporating proximity technologies in a logging machine or personal equipment, and enhancing logging machine design to enhance safety, ergonomics, and SA.