In Best Month Ever!, players take part in a roller coaster of emotions with Louise, a mother embarking on a road trip of a lifetime through the late 1960s USA. She is trying to show her son Mitch how to navigate the often cruel modern world by making crucial choices that may change their lives for good, and influence what kind of person Mitch turns out to be. Along their journey they meet various characters who can either help or dissuade them from reaching their goals, teaching Mitch the values he needs to become independent and brave enough to conquer the day.