Onward to Calgary follows a public access poetry show host (Jim Ether) through the aftermath of a poor business decision. After signing a document allowing the unscrupulous Bronson Fish Stick and Fish Cake Co. to advertise on his show "Poem Time", it becomes apparent that the companies motives are to completely dominate the poetry empire Jim has worked so hard to build. At his wit's end, Jim receives a letter from a female fan of the show which illustrates her desire towards one of the shows co-hosts, a talking tomato named Timmy. With a strong desire to escape the situation Jim's created for himself, uniting Timmy tomato with his fan seems like a great excuse to get the hell out of dodge. What follows is a departure from the familiar and comfortable into the "real world" where it's quickly revealed there was a lot more in the fine print of that contract than he bargained for.