Although Douglas was born when the railroad came through in 1886, it never quite managed a true "hell on wheels" atmosphere.  Twenty-five saloons opened in 1886, but only six survived to the end of the year.  The local bad boys were known more for cattle rustling than murder, and since Douglas was definitely on the side of the small ranchers during the Johnson County War, cattle rustling was considered a very minor crime.

Well-liked cowhand George Pike was so adept at roping and branding unsuspecting mavericks that local ranchers vied to keep him in their employ, where they would benefit rather than suffer from his skills.  One story has him in a saloon in Douglas, losing money at a crooked poker game.  When he realized why he was losing so consistently, Pike left the game.  Shortly thereafter a "hobo" held up the game and relieved the cheating player of $2,500.  As soon as the "hobo" left, Pike returned dressed as himself to sympathize with the victim.

Another lighthearted tale takes place in Douglas' first jail, a remarkably stout building with a chrome steel cage.  Its walls, ceiling, and floor were made of planks six inches thick, and eight inches of brick covered the outside of the building.  It was considered escape proof, but one prisoner almost made it out.  He pried up some floor boards and dug a tunnel to the alley behind the jail.  Unfortunately for him, he surfaced inside the territory of a chained bear owned by an old trapper living next door.  His welcome was so unnerving that he decided he’d rather face justice in jail.

Douglas also played several minor roles in Johnson County War stories.  The two trappers who witnessed the murders of Champion and Ray were kept in protective custody in the Douglas jail, since it was considered the most secure one around.  The extremely powerful cattle barons however, hired O. P. Witt (a Douglas livery stable owner) and F. H. Harvey (a Douglas lawyer) to break them out of jail and escort them east so they couldn't testify in court.  Douglas in general was on the side of the Johnson County defenders.

Lee Moore, whose descendants still ranch in the area, sent his wife and children back to Texas when he learned he was on the invader's hit list.  He took to hiding out, moving to a new campsite each night.  He was present at the standoff at the TA Ranch and retrieved Nate Champion's rifle from the invaders’ wagon.  You can see it now at the Pioneer Museum in Douglas.

Dr. Penrose, who had so blithely volunteered his physician's services to the cattle barons, escaped arrest at the TA Ranch and took refuge in Douglas where he almost got himself hung.  Luckily, then Wyoming Governor Amos Barber had graduated from the same medical school as Penrose and sent a marshal to "arrest" him and ship him east on the next train.

Douglas is extremely proud of its mythological beast, the jackalope.  You can't drive through Douglas without glimpsing a statue of one, and if you want, you can stop and buy a jackalope hunting license.

Douglas is the home of the Wyoming State Fair which has packed the town one week each summer since 1905.

During World War II Douglas hosted a large POW camp, but the only remnants left today are the murals that Italian POW's painted in the old officer's club, now the local Odd Fellows Hall.