Keep in mind is that the "Wild West" was generally not as lawless as Television and Movies have led us to believe. Most settlers, and thus small towns, were pretty peaceful, looking for a quiet place to live, to farm, to raise a family, and maybe make a few bucks along the way. Roving gangs of robbers were not a regular occurrence. Most of those that existed only had a few members and were usually caught pretty quickly as a group.

Of course... all those stories do have a grain of truth in them.

My area of expertise is Oregon and the Oregon territory, so I am not able to write specifically about other Western States. Generally most Oregon small towns didn't have a jail at all unless they were the county seat. I can not think of more than a few outlaw gangs of the type you're asking about, and none that were not apprehended (or killed,) together who would have left members capable of breaking them out.

The Oregon Territory, before it became a state, had a roving Judge and a Marshall, but most of their work was administrative not law enforcement. Even then most punishments were financial because they didn't necessitate jail time. I can not think of many cases of "frontier justice," although I would not be surprised to find it happened more than we know.

The US Army had a significant presence to enforce laws on the Indian Reservations and to protect the Indians from Settlers, and Settlers from Indians. The forts on the reservations would usually use their stockade or guard house as a makeshift jail as needed. Their prisoners were usually soldiers found derelict of duty, or Natives who had left the reservations without permission or who had been caught stealing.

Gold Rush towns and Timber Towns tended to be the most lawless, but it was rarely anything major. These towns would usually all have a jail building made of wood or stone, but were frequently unguarded over night unless there was an high value prisoner inside. Most issues were public drunkenness or drunken disagreements that got out of hand. Drunks were thrown in jail to sleep the alcohol off and peacefully let go in the morning.

There was an noteworthy escape from the Oregon State Penitentiary that had no outside help. That directly led to the creation of the "Oregon Boot" in the 1860s to help make escape harder, but I do not know how wide spread its use was outside of Oregon. It did see some use up in Seattle and San Fransisco, and as far east as Boise, but the Oregon State Penitentiary was by far the biggest user until WWI when it was finally retired from common use.

Golden Oregon, now an Oregon State Park, fixed the issue of lawlessness simply by being founded by a rather stern religious figure who frowned upon any vices in his town at all. All the miners would walk several miles on payday to spend their money in the next town over. Neither city had a jail, so drunks were usually left in the woods between the two towns to sleep it off.

Goble Oregon, an timber town on the lower Columbia River, has a story of drunken loggers being imprisoned overnight in the town jail. They escaped by breaking up the wood floor with their cork boots.

Oregon's first murder, Nimrod O'Kelly, was simply locked up in his neighbors shed for a few months until the judge came around to pass sentence. After that he was sent to the new jail built in Portland. He was handcuffed to the wagon that transported him to the jail, but funny enough the Deputies who were escorting him both got drunk and fell asleep in the wagon. O'Kelly ended up driving the wagon to Portland himself. He wasn't a violent man though, the murder was an accident. Two other settlers would not accept his land claim and had staked out their own claims over his. The shotgun he was holding went off by accident when he confronted them for the hundredth time, killing one of the men. It was later conclusively proven that O'Kelly's claim was indeed valid.

Danford Balch, who murdered the neighbor boy who had eloped with his daughter, also escaped jail by breaking through the rotted wood of the jail cell. He hung out on his own land for several months until he was recaptured in the summer. Portland's first Police Chief, who happened to also be a crooked saloon owner, let it be known that he was amendable to a $1000 bribe to leave Balch's jail cell unlocked the night before he was to hang. Danford's wife wasn't able to raise the bribe money in time, and Balch became Portland's first hanging.

His name escapes me right now, but in Lakeview Oregon, a man was jailed for beating his horse and his wife (in that order specifically, and the horse was only beaten two or three times where as the wife had endured it for years.) He was not a well liked person even before that though. A mob broke him out of jail and lynched him. The deputy guarding the jail at the time stood back and let it happen, but committed suicide over his inaction about two decades later.

Another common punishment was being impressed into a merchant ships' crew. In port cities, specifically Portland and Astoria, merchant captains were frequently so hard up for crew members that they'd take anyone they could. Crimpers would abduct sailors in broad daylight and sell them to captains desperate for crew. But Captains would also scour the local jails for anyone vaguely able bodied, frequently paying off fines and debts to do so. Prisoners would walk to the ships in chains under guard of police, US Marshals, or hired guards, then locked below deck until the ship had sailed out of sight of land.

The escape that resulted in the murder of Sheriff Til Taylor in Umatilla County involved the girlfriend(wife?) of one of the escapees smuggling a gun into the jail. That was towards the very end of the Wild West time period, in the 1920s. Sheriff Taylor is still a well known figure in the community and an annual rodeo is held in his honor.

The last tale I can think of in this vein would be that of Miss Fern Hobbs, Governor Oswald's secretary who was sent with six Oregon National Guardsmen to impose martial law on the town of Copperfield Oregon. They shut down three saloons in town that had been increasingly breaking the law to keep profits up in light of a dwindling town population, including selling to minors.