This paper explores trends in summer and intermittent teaching practices among African American students in the post-Civil War South, focusing on student activities in the field, the institutions they attended, and the communities they served. Transitioning out of the restrictions and impoverishment of slavery while simultaneously seeking to support themselves and others was an arduous and tenuous process. How could African American youth and young adults obtain the advanced education they sought while sustaining themselves in the process? Individual and family resources were limited for most, while ambitions, both personal and racial, loomed large. Teaching, widely recognized as a means to racial uplift, was the future occupation of choice for many of these students.