The narrator reminisces about falling in love with an outlaw highwayman on the road to Fairfax County. They shared a brief romantic encounter under an oak tree, planned to elope to a far island, but their love was discovered by the sheriff who ends up hanging the highwayman on the same oak tree where they made love.

Meaning of "On the Road to Fairfax County" by The Roches

The lyrics of "On the Road to Fairfax County" explore the themes of forbidden love, betrayal, and the harsh consequences of going against societal norms. The narrator's relationship with the outlaw highwayman symbolizes the idea of passionate love that transcends boundaries and rules. Despite the risks and dangers involved, they were willing to defy conventions in pursuit of their love. However, the intrusion of the sheriff represents the harsh reality that society often punishes those who do not conform. The tragic ending underscores the idea that love can come at a high price, and that going against the grain sometimes leads to devastating consequences. Overall, the song paints a poignant picture of star-crossed lovers caught in a world that will not allow their happiness.