Dear Sidewalk tells the story of Gardner, a 24 year old mail-carrier, who is struggling to contend with his identity as his quarter-life crisis is in full swing. His regimented routine is thrown out the window when he meets Paige, a divorcee, enduring a mid-life crisis of her own. In this relationship there exists a synchronicity, as they find, despite their age difference, they're both confronting existential problems surrounding identity, love, and the choices in front of them.

Four actors go to a cabin in the woods to write, direct, and act in a film that will jump-start their careers. Their idea is a horror film about a man with a bag over his head, but what happens when that man mysteriously shows up?