ABSTRACT Introduction: Trauma history is a major risk factor for homelessness because of debilitating mental health and trauma symptoms that reduce a survivor’s ability to maintain healthy psychological functioning. Method: The objective of this study was to explore trauma exposure among a group of homeless mothers (N-30) using a novel data-gathering tool, the Life History Calendar (LHC). Participants completed a questionnaire consisting of several standardized scales and participated in a 90-minute LHC interview. Results: All participants (100%) reported at least one type of trauma experience in their lifetime; the majority (76.6%) reported an unstable and chaotic home environment and bullying and teasing as significant traumatic stressors. Other reported stressors included witnessing violence, intimate partner violence, grief and loss, childhood sexual abuse, physical/emotional/verbal abuse, and sexual assault. Participants completed a questionnaire that assessed psychological symptoms; 77% met the criteria for major depressive disorder and generalized anxiety disorder, and 42.3% endorsed severe PTSD symptoms. Conclusion: This study increases our understanding of the traumatic experiences of a group of homeless mothers by identifying critical periods in their lives when their traumas occurred. Supporting at-risk groups during these periods can play a significant role in averting their trajectory toward homelessness.