At some point in our lives, we all step across that proverbial line where the road ahead of us is suddenly, and sometimes, shockingly, shorter than the one we have been traveling. It's a visceral and profound moment, often times bringing on the mid-life crisis, where one realizes that over half of their time on Earth has passed. Trent McCallister, born and raised on a cattle ranch in Alberta, Canada, eventually morphs from the life of a cowboy to a white-collar job with the Canadian Embassy. A family man, whose children are now out on their own, Trent finds himself facing the specter of imminent death up ahead. He hasn't achieved most of his dreams and finds himself trying to reconcile his life. He decides on a reprieve to Rhodes, Greece, where he rents a boat and heads out for a sail, a day that would change his life. When Cowboys Fall is a story about rediscovery, following one's dreams, and love - a story about the cowboy in all of us.