This article depicts a qualitative narrative study that reflects on the educational paths followed by three generations of Black women from rural Mississippi. The purpose of this study was to expand the documented footprint of Black women's educational experiences in the rural Deep South by exploring my own educational experiences as a researcher and as a participant as well as the experiences of women in my immediate family. Reflections, connections, and analyses address 20 years of lived experience in Mississippi school systems. The intersectionality of critical race theory (CRT) rooted in Black feminist theory provided the theoretical framework. The research questions addressed were: What are the similarities and differences among three generations of Black women educated in Mississippi? How can this information assist us to better understand the historical and present intersectional struggles of Black education in rural areas? The intersections of gender and race were explored. Mapping as inductive analysis using writing as inquiry allowed me to garner a deeper meaning of the stories. The approach to story analysis was iterative as I moved in and out of several steps. My insights and reflections depicted a supportive village that helped to guide the women through their studies. The overall finding was that these women's sustained success in rural Mississippi educational settings was linked to having a nurturing and supportive network of educators throughout their academic careers. We need to investigate other Black women's educational experiences in rural education settings to increase representation and to demonstrate the congruences and particularities of learning what matters to Black women in rural communities.