The purpose of this study is to give voice to African Americans who were students in Randolph County during the desegregation of its schools. The introduction identifies the roadblocks African Americans faced that restricted their acquisition of an education. It starts by discussing the legal battles associated with the attainment of a public education such as Plessy v. Ferguson, 163 U.S. 537 (1896). This study also discusses the reaction of African Americans to the Plessy v. Ferguson, 163 U.S. 537 (1896) and the questions of educational equality associated with the decision of Brown v. Board of Education of Topeka, 347 U.S. 483 (1954). A brief synopsis of Randolph County Training school is presented along with information about the efforts of Randolph County’s African American citizens to enter into previously all white schools. Information is included that discusses the efforts of Randolph County’s school board to avoid complete school desegregation by implementing what was known as the Freedom of Choice Plan in 1965. There is also a small discussion of the History of Randolph County Training School that includes information about its founding, its curriculum, and the level of success acquired by some of its prominent students. This study utilizes the framework of Critical Race Theory and Narrative Analysis to examine the students’ perceptions of their experiences in segregated schools, during the Freedom of Choice Movement, and the last phase of the desegregation procedures which occurred in 1970. This research provides a history of the desegregation procedures of Randolph County and brings focus to the what the community, students, and faculty lost during desegregation by presenting a narrative that focuses not on the deprivation associated with segregated schools, but the achievements of the faculty and students against insurmountable odds.