America, 1899. The End of The Wild West Era has Begun. After a robbery goes badly wrong in the western town of Blackwater, Arthur Morgan and the Van der Linde gang are forced to flee. With federal agents and the best bounty hunters in the nation massing on their heels, the gang must rob, steal and fight their way across the rugged heartland of America in order to survive.

Looking for information on the O'Driscolls' planned train job, Dutch leads the gang into an attack on their camp. With the gang low on supplies and starving, Mr. Pearson sends Arthur and Charles out hunting.

In need of money, and with the plans and explosives stolen from the O'Driscolls' camp, the gang ride out to rob Leviticus Cornwall's private train. With renewed strength and the weather finally stable, the gang ride down from the mountains to set up camp at Horseshoe Overlook.

In search of new leads for the gang, Karen, Tilly and Mary-Beth convince Arthur and Uncle to ride out to Valentine with them. Bill starts a brawl in Smithfield's Saloon in Valentine as Javier, Charles and Arthur attempt to charm the locals.

After spotting a huge bear up by the Dakota River, Hosea and Arthur ride out and track it.

Under the threat of torture, Kieran leads Arthur, John and Bill out to Six Point Cabin where he claims Colm O'Driscoll is holed up.

Following a tip from the Valentine Sheriff, Arthur attempts to capture and turn in Benedict Allbright, a wanted criminal, out near the Dakota River. Arthur takes Lenny for a quiet drink in Valentine to help to calm him down after learning of Micah's arrest in Strawberry.

Arthur attempts to reclaim the debt from debtors including Thomas Downes but finds him to be destitute.

An old friend from Arthur's past needs his help to find her brother who's ran away from home to join a Chelonian religious cult.

With Micah due to be hanged for a double murder near Strawberry, Arthur attempts to break him out of jail.

Following a tip-off on Sean's whereabouts, Arthur, Trelawny, Javier and Charles track Ike Skelding's bounty hunters up the Upper Montana River and attempt to rescue Sean.

To prove their business credentials to the Emerald Ranch fence, Seamus, Arthur and Hosea attempt to rob a stagecoach from Old Bob Crawford at Carmody Dell.

Charles and Arthur go hunting for the greatest of gifts, Bison.

Arthur does a favor for Abigail and takes Jack out on a fishing trip. Blocking the tracks with the heavy oil wagon, Arthur, John, Charles and Sean board the train and rob valuables from the rich passengers and baggage car.

Following a tip-off, Micah and Arthur rob a banking stagecoach.

John has a plan to rustle a herd of sheep and sell them at auction in Valentine.

Wanting the gang to lie low after the trouble in Valentine, Dutch asks Arthur and Charles to scout out a new camp location at Dewbury Creek.

Arthur, Dutch and Hosea go out on a fishing trip.

To get her out of camp for a while, Arthur takes Sadie into Rhodes to collect supplies.

A man called Margaret, who's needs Arthur help to find his runaway circus animals.

Arthur and friends go on a fishing trip.

Strauss gives Arthur two names of the men he needs to collect money from. The first one, a unemployed man named Winton Holmes, is located in a camp north of Strawberry and is unable to pay back his debt. The other, Gwyn Hughes, is an undertaker apprentice who is unable to pay back his debt.

Arthur, Dutch and Bill become temporarily deputized citizens of Scarlett Meadows County as they help Deputy Archibald shut down a moonshine distillery and steal a wagonload of the Braithwaites' moonshine.

Uncle receives a tip-off and rides out with Arthur, Charles and Bill to rob a wagon carrying payroll. With the heat in Valentine having died down, Bill thinks it's finally time to hit the bank. Karen causes a distraction while Arthur handles the vaults.

Beau Gray asks Arthur to deliver a letter to Penelope Braithwaite at Braithwaite Manor. At the request of Beau, Arthur drives Penelope and other protestors through Rhodes as they participate in a women's suffrage rally.

Catherine Braithwaite pays Hosea and Arthur to head into Rhodes and hand out the stolen moonshine for free at the local saloon. Arthur and Charles go to track down Trelawny at his rental caravan in Rhodes. Trelawny causes a distraction as Arthur robs a stagecoach in Scarlett Meadows following a tip-off from a discouraged worker at Rhodes post office.

To get back at the Braithwaites, Tavish Gray asks Arthur, John and Javier to steal prized horses from Braithwaite Manor that he claims will sell for $5000. Working with the Braithwaites, Arthur and Sean drive to Caliga Hall with the remaining moonshine and attempt to use it to help burn the Grays' tobacco fields.

Suspecting a trap, Micah asks Arthur to observe an arranged meeting between Dutch and Colm O'Driscoll from afar.

Arthur, Micah, Bill and Sean go to meet some of the Gray boys in Rhodes to discuss a security job. Suspecting it was Catherine Braithwaite who kidnapped Jack, Dutch, Arthur, John and the gang ride to Braithwaite Manor to get him back. John and Arthur clear out the last remaining Lemoyne Raiders from Shady Belle before the gang relocate their caravan.

Having just arrived in Saint Denis, Dutch and Arthur ask around the Bastille Saloon for information on Angelo Bronte. John, Dutch and Arthur head to Bronte's mansion to get Jack back. Bronte asks the gang to clear out the local graveyard in return for Jack.

Mary asks Arthur for help with her father, who has become consumed by a gambling addiction. Arthur must retrieve a valuable family heirloom Mary's father has sold off.

Susan and Arthur head to the Foreman Brothers' hideout to rescue Tilly, who has been kidnapped.

The gang attend a party hosted by the Mayor of Saint Denis. While at the party, they meet with Bronte, and look for job opportunities.

Brother Dorkins asks Arthur to investigate a nearby shop suspected of acting as a front for human trafficking. While at the Mayor's party, the gang learned of a card tournament being held on the Grand Korrigan riverboat. Strauss and Trelawny fix a game so Arthur can win big on the tables.

A street kid steals Sister Calderon's crucifix. Arthur chases the kid through the streets of Saint Denis to get it back.

The O'Driscolls send Kieran's mutilated body to the gang camp at Shady Belle, before launching a brutal attack. Arthur meets Eagle Flies outside Cornwall Kerosene and Tar, and prepares to break in to steal a report on the oil reserves at the Wapiti Reservation. After receiving a tip from Bronte about a trolley station in Saint Denis holding a large amount of cash, Dutch, Arthur and Lenny meet to rob it.

Before they can rob the Saint Denis bank, Dutch convinces Arthur that they must kill Bronte. They visit Thomas, a local fisherman, to procure a skiff for the assault on Bronte's mansion. The gang attacks Bronte's mansion from the river to get rid of the threat of Bronte's men and to take revenge for the trolley station setup.

In order to fund their escape and retirement abroad, the gang prepare for one last job, robbing the bank of Saint Denis.

Having survived the shipwreck, and now washed ashore on a remote island, Arthur begins searching for the gang. In order to secure safe passage off the island, Arthur has agreed to rescue some local workers for Hercule and Leon With the help of a local, Gloria, Dutch and Arthur infiltrate Fussar's compound to rescue Javier. The gang meet Hercule at the fortress of Cinco Torres and prepare to clear the waters around the island so they can safely depart for America. Arthur and the gang must destroy gun emplacements on the coast, and rescue the ship captain, before they can leave the island.

Arthur heads for Shady Belle to try to track down the rest of the gang. Arthur is reunited with the gang at Lakay. Milton arrives with his Pinkertons, and attacks the camp. Dutch sends Arthur and Charles to Beaver Hollow to find a new location for the gang's camp.

Arthur passes out in Saint Denis, and wakes up to find a stranger dragging him to the doctor's surgery. Sadie's contact, Mr. Bullard, agrees to take Arthur in his hot air balloon to scout out the Sisika Penitentiary. Arthur and Sadie row to Sisika Island to break John out of prison.

Leopold Strauss needs Arthur to collect two debts, one from J. John Weathers and another from Arthur Londonderry.

Arthur tries to help Penelope Braithwaite and Beau Gray escape their families. Edith Downes tells Arthur that her son, Archie, is working at the Annesburg Mine. Arthur heads to the mine, to find Archie being goaded by the foreman, Mr. Dockery. Arthur meets Dutch and Micah in Annesburg where they are planning to confront Cornwall.

Unwilling to accept Arthur's money, Edith Downes continues to sell her body. Worried for his mother's safety, Archie Downes asks Arthur to head to Willard's Rest to look for her.

Eagle Flies and the gang launch a raid on an army boat, to reclaim horses stolen from the Wapiti Reservation. Bill and Arthur ambush an army convoy transporting dynamite through Van Horn. With Colm O'Driscoll under arrest, Sadie, Arthur and Dutch head to Saint Denis to watch him hang.

John and Arthur plant dynamite on the Bacchus Bridge in order to create a distraction and disrupt the army's transportation. Arthur visits Rains Fall in Wapiti and they travel to a sacred Native American site in the East Grizzlies.

Colonel Favours is redirecting smallpox vaccine away from the Wapiti Reservation to punish the Native Americans for the recent unrest. Monroe requests Arthur's help to steal the vaccine from the army. Arthur attends a truce meeting between Colonel Favours and Rains Fall, where Rains Fall hopes to negotiate peace. Arthur and Sadie travel to Hanging Dog Ranch to finish business with the O'Driscolls once and for all.

In order to draw attention away from the gang and onto the Natives, Dutch convinces Eagle Flies to ambush an army patrol. Upon learning that Eagle Flies has been captured by the army, Arthur and Charles infiltrate Fort Wallace to rescue him. Eagle Flies rides into Beaver Hollow to rally support for a final attack on Cornwall Kerosene and Tar. Against Rains Fall's wishes, Dutch and the gang accompany Eagle Flies into battle against the army.

As their final job, the gang ride to Saint Denis to intercept and rob a train carrying army supplies and payroll, headed for the recently destroyed Bacchus Bridge. With John assumed dead, and Abigail captured by Pinkertons, Dutch cuts them loose, and rides for Beaver Hollow. Arthur and Sadie head to Van Horn to rescue Abigail.

Several years after fleeing Dutch and the gang, John, Abigail and Jack look for work in the town of Strawberry. Using the pseudonym 'Jim Milton', John has secured a job as a hand at Pronghorn Ranch, and gets to work. John works a day at the ranch, helping Dickens build a fence, and looking after livestock. With the other ranch hands busy, and Geddes heading in to town, John takes on more work on the ranch. A gang of hired-guns cause trouble on Pronghorn Ranch. John juggles fatherhood and his multiple identities as he heads to Strawberry with Jack to collect mail for Geddes, and a package for Abigail. John is thanked by Mr. Geddes for his help with the Laramie Gang, and he turns in for the night, only to be woken by a raid on the ranch.

John receives a telegram from Sadie Adler. Before he can purchase Beecher's Hope, John must inspect the land and move on any illegal tenants. Back in Blackwater he runs into an old friend.

After receiving a telegram from Sadie, John meets her in Valentine and helps her with some bounty hunting work. Uncle tells John that he has heard that Charles Smith is alive and in Saint Denis. John and Uncle go to Saint Denis to track him down. John, Uncle and Charles tear down the derelict shack at Beecher's Hope. John meets Sadie in Blackwater. Sadie asks John to help her recover a bounty named Shane Finely who was taken from her by a professional rival, James Langton.

John puts together his pre-cut ranch house with the help of Charles and the encouragement of Uncle.

With his debts mounting and a barn to buy, John accompanies Sadie to hunt down the wanted criminal, Ramón Cortez, and bring him to justice. Uncle, John and Charles spend the night celebrating after finishing work on the barn. John wakes to find Uncle has been taken by the Skinner Brothers.

Sadie visits John at Beecher's hope. They leave to hunt down a bounty, Marshall Thurwell, in Tall Trees and discuss other men who have evaded their capture. John takes Jack fishing with the family dog, Rufus. They catch more than they bargained for. John and Abigail go in to Blackwater to spend some quality time together. John has a question to ask

Sadie has a clue that might lead them to Micah - Cleet has been sighted in Strawberry. Despite Abigail's protests, John, Sadie and Charles ride there to interrogate him and track down their old enemy.