Town College City Road follows Kurt Boozel from childhood in an insular Northwestern Pennsylvania steel town through life's booms and busts, and back to his Rust Belt home. As a teenage math whiz, Kurt is bullied but relishes the opportunity to tutor his high school's star athlete. After their friendship ends in a public and emasculating act of violence, Kurt steers his life progressively eastward, first as a closeted economics major clinging to the coattails of his richer fraternity brothers, then to New York for a high-pressure finance job. After turning his attention to the fantastic promises of the cryptocurrency market, he finds himself unmoored while driving across Pennsylvania in the midst of a snowstorm to be the best man at his brother's wedding.

Through his struggles to pass multiple masculine initiations, both real and metaphorical, Kurt ultimately discovers that the only thing tougher than running away from rural mythology is constructing a new one.