Lyric discussion by AndreAndre 

Cover art for Trials & Troubles lyrics by Old Crow Medicine Show

this is my favorite song by old crow. It think it's pretty apparent what the song's about. his girl was "a ramblin gal bound to leave her home" and she set out walking down the railroad track. she got her foot stuck in a hole (possibly breaking her ankle or something). The train was coming too fast around a bend (Round the bend at 40 miles) so it came upon her suddenly, and it couldn't stop quickly enough (20 tons of loaded frieght a-comin' on) and she was stuck on the tracks and got run over by the train. so now he's decided to "ride that line Till I see that black train come" - meaning he's going to be a hobo, ride the train lines, until he dies. He's going to "buy them all Cigarettes and chewing tobacco" when he can instead of saving up his money because he now sees how close death is and is not too concerned about the future. As to the brown skin part, maybe she was an african american. It doesnt have to mean she was a slave.

by the way, chapel hill is chapel hill, North Carolina, one of the most beautiful towns in the nation. So by making that reference he's giving the idea of how far the train travels.