[3]: 49  At the age of 16, she was enrolled in a boarding school where she became enamored with a young man, named Hart, who has been variously described as a rake, drunkard, and/or gambler.

Pearl in turn developed a fascination with the cowboy lifestyle while watching Buffalo Bill's Wild West Show.

[4] At the end of the Fair, Hart left her husband again on a train bound for Trinidad, Colorado, possibly in the company of a piano player named Dan Bandman.

[3]: 53–54  The novelty of a female stagecoach robber quickly spawned a media frenzy and national reporters soon joined the local press clamoring to interview and photograph Hart.

[6] One article in Cosmopolitan said Hart was "just the opposite of what would be expected of a woman stage robber," though, "when angry or determined, hard lines show about her eyes and mouth".

[4] Taking advantage of the relatively weak building material, and possibly with the aid of an assistant, Hart escaped on October 12, 1899, leaving an 18-inch (46 cm) hole in the wall.

Judge Fletcher M. Doan was shocked and angered when the jury found her not guilty and scolded the jurors for failure to perform their duties.

The warden, who enjoyed the attention she attracted, provided her with an oversized 8 by 10 feet (2.4 by 3.0 m) mountainside cell that included a small yard and allowed her to entertain reporters and other guests as well as pose for photographs.

[4][6] Hart, in turn, used her position as the only female at an all-male facility to her advantage, playing admiring guards and prison trusties off of each other in an effort to improve her situation.

[6][11] Pearl Hart was the main character, played by Anne Francis, in a Death Valley Days episode “The Last Stagecoach Robbery” aired March 17, 1964.

The episode centered on the holdup committed with Joe Boot and their subsequent capture portraying her as adventurous but kindhearted in her search for notoriety.

Hart is portrayed as a "real Wild West legend" compared to the fictionalised antics of Billy the Kid and Wyatt Earp.

For another account of her life, see: "Pearl Hart and the Last Stage", short story by Edward D. Wood, Jr. published in Outlaws of the Old West, a collection of selected readings by Mankind Magazine, edited by Charles D. Anderson, 1973