Welcome to Winding River, Wyoming, home to the Calamity Janes , five friends who have stuck together through every high and low through out their lives and the different directions they all have traveled. When it's time for their high school reunion, Cassie, Karen, Gina, Lauren and Emma all head home to be together. And for the changes that are to come.
Ten years ago Cassie Collins fled Winding River pregnant and alone after Cole Davis left her without a word. In the years since she has tried her best to raise their son, Jake, the best she could. Only going home for rare and brief times, Cassie has lived with the fear that Cole would one day find out about Jake and want to claim him. Once she receives the reunion invitation, Cassie isn't sure she should go, despite Jake begging to go for this visit. When Jake gets into trouble, Cassie is persuaded that going home may be for the best.
Cole Davis has never gotten over Cassie. When he was forced by his father to leave her behind, he tried to explain in a letter, and asked for her to wait for him. The answer was she never wanted to see him again. Yet he's still never moved on and wonders if he ever will. But when the high school reunion brings Cassie home, and his father pushes him in Cassies direction, even after forcing them apart, Cole can't help but wonder what is really going on.
With secrets they must uncover to get to the truth and to be able to start over, Cole starts his campaign to get a second chance with Cassie. Except Cole isn't prepared for the biggest secret of all; that Jake is his son. Can he ever forgive Cassie for keeping his son from him? Can the Calamity Janes help their friends through one of the hardest times and still be there for one another? Or will Cole decide this is just one betrayal he can't move past and loose Cassie for good?