"Two Girls and the Doolin Gang" is very loosely based on actual events and is about Annie McDoulet and Jennie Stevens, two adolescent girls traveling through Oklahoma Territory in the late 19th century in search of excitement and adventure. Annie is fascinated by the stories she reads about the western outlaws, especially those about Bill Doolin, but when they finally catch up with his gang, they realize that the men are old, haggard, tired, and only ever one step ahead of the relentless pursuit of famed western lawman Bill Tilghman.