A "songster" is a wandering musician, usually but not always African-American, of the type which first appeared in the late 19th century in the southern United States.
Songsters in American culture
The songster tradition both pre-dated and co-existed with blues music. It began soon after the end of slavery and the Reconstruction era in the United States, when African-American musicians became able to travel and play music for a living. Black and white musicians shared the same repertoire and thought of themselves as "songsters" rather than "blues" musicians.
Songsters generally performed a wide variety of folk songs, ballads, dance tunes, reels and minstrel songs. Initially, they were often accompanied by non-singing "musicianers", who often played banjo and fiddle. Later, as the guitar became more widely popular, the songsters often accompanied themselves.