This is an exploratory qualitative study based on the personal experiences and observations of 23 research participants made up of leaders of Christian, Jewish, and Muslim faith organizations. As such, data generated through this study is not meant to quantify or compare differences between the three faith communities involved. This research project focused on (1) understanding what is happening with interfaith dialogue in Winnipeg from the perspective of leaders of Christian, Jewish, and Muslim faith-based organizations (FBOs), (2) identifying obstacles to interfaith dialogue among Abrahamic faith organizations in Winnipeg, and (3) identifying perspectives on the potential benefits of interfaith dialogue among Abrahamic faith organizations in Winnipeg. The research is based on semi-structured one-on-one interviews with leaders of Abrahamic FBOs and the drawing of a personal lifeline identifying landmark events related to faith and interfaith involvement in participants’ lives. The study is rooted in grounded theory and arts-informed methods as the two main inquiry approaches to research. The stories and lifelines generated through these interviews were then analyzed for common themes and data was compiled based on details identifying the occurrence of interfaith dialogue in the city and its perceived obstacles as well as benefits among Winnipeg’s Abrahamic faiths. The data was then used to generate findings, and to propose potential areas for future action and research. The research is framed by Peace and Conflict Studies (PACS) literature on Critical and Emancipatory Peacebuilding, Interfaith Dialogue, and Conflict Transformation to situate the study. By combining an understanding of Winnipeg’s context with the literature and data on interfaith dialogue and peacebuilding, the research explores what is happening with dialogue between religious organizations, what barriers may be preventing dialogue, and what level of willingness exists for FBOs to participate in dialogue.