The Dear Hunter started as a solo side project by singer and keyboardist Casey Crescenzo, formerly a key member of Belchertown, Massachusetts emo act the Receiving End of Sirens. An outlet for Crescenzo's songs that didn't fit the Receiving End of Sirens' heavy post-hardcore vibe, the Dear Hunter was initially envisioned as a concurrent project. Indeed, Crescenzo's first gig as the Dear Hunter was an opening slot for the Receiving End of Sirens, at which he was backed by the other members of the band. Shortly afterward, however, he decided to leave the group and focus full-time on the Dear Hunter.
Following a self-released EP taster called Dear Ms. Leading, Crescenzo wrote and recorded the full-length concept album Act I: The Lake South, The River North, which starts with the story of a young boy's birth at the dawn of the 20th century and his relationship with his mother.