Trauma history is a major risk factor and pathway to homelessness due to debilitating trauma-related symptoms that reduce a survivor’s ability to maintain healthy psychological functioning. The objective of this study was to explore common experiences of trauma exposure among women (N-30) living in an urban Mid-Atlantic city in the United States who are or were recently homeless using the Life History Calendar (LHC). Research participants completed a questionnaire that assessed symptoms of depression, anxiety, and trauma before participating in interviews. The LHC assisted participants in recalling significant events over their lifetime. Domestic violence and community violence were reported as primary traumatic stressors; bullying/teasing and childhood sexual, physical, and emotional abuse were secondary stressors. Qualitative data-gathering methods such as the LHC provide important insights that are often not easily available through quantitative aggregated health service data. This study increases understanding of the traumatic experiences of a specific group of homeless mothers living in an urban environment. It identified critical periods in their life when traumas occurred. Supporting at-risk groups during these critical periods can play a role in averting a trajectory toward homelessness.