The prevalence of burnout and depression are high among surgical trainees. This study examined the impact of program-driven initiatives to improve surgical trainee wellness. A survey was administered to residents and fellows at all surgical training programs across an urban academic health system. The survey measured burnout, depressive symptoms, and perceptions of program-driven wellness initiatives. The response rate was 44% among 369 residents. Of these, 63.2% screened positively for burnout, and 36.7% for depression. Residents who were burned out were more likely to work >80 h per week, have greater clerical duties, and miss educational activities more frequently. Conversely, having opportunities for wellness activities, dedicated faculty and housestaff wellness champions, and assistance with clerical burden were all associated with lower rates of burnout and depression. The presence of wellness support was associated with better outcomes, suggesting the value of initiatives to manage workload and support the well-being of surgical resident physicians. •Burnout and depressive symptoms are prevalent among surgical trainees.•Training program-driven wellness initiatives can support trainee well-being.•Depression may be difficult to predict from individual- and program-level factors. The present study measured the prevalence of burnout and depressive symptoms among surgical residents and fellows across an urban academic health system. Prevalence of burnout and depression were 63.2% and 36.7%, respectively. Greater workload appeared to be correlated with increased burnout and depression, whereas the presence of program-driven wellness initiatives was associated with better wellness outcomes.