Background: The aging prison population in the United States presents a significant public health challenge with high rates of trauma and mental health issues that the correctional system alone is ill-prepared to address. The purpose of this study was to examine the relationship of age, objective, and subjective measures of trauma and stressful life events and post-traumatic stress symptoms among older adults in prison. Methods: Data were gathered from 334 prisoners (aged 55+) housed in the New Jersey Department of Corrections, as of September 2010. An anonymous self-report, self-administered survey was mailed to the total population of 1,000 prisoners aged 55 years and older. Objective and subjective trauma was measured using the Life Stressors Checklist-Revised (LSC-R), and post-traumatic stress symptoms were measured using the Civilian Version of the Post-traumatic Stress Scale. Findings: Results of a path analysis revealed that past year subjective impressions of traumatic and stressful life events had a positive and significant relationship to current post-traumatic stress symptoms. Age was found to have a significant and inverse relationship to subjective traumatic and stressful life events. That is, younger participants reported higher levels of cumulative traumatic and stressful life events and past year subjective ratings of being bothered by these past events. Implications: These findings have significance for interdisciplinary/interprofessional practice and appropriate institutional and community care, including reentry planning of older adults in the criminal justice system.