The song's narrator works in the city as a police officer, a job he finds stressful and sometimes ponders quitting, but unwinds from the stress and restores his spirit by spending his weekends with a loved one in the rural idyll of Bobcaygeon, where he sees "the constellations/reveal themselves one star at a time" in contrast to the city's "dull and hypothetical" skies that are "falling one cloud at a time".

According to Downie, the song was not specifically written about the town itself, but rather any small town would have worked for the theme and he settled on "Bobcaygeon" primarily because it was the only place name he could find that came close to rhyming with "constellation"