The Winter War was a conflict in The North fought between the forces of House Baratheon under Stannis Baratheon, House Bolton and various other houses of the North loyal to House Stark. It was fought between the years 300 - 302 AC and was part of the larger War of the Five Kings.
The Long Road Ahead Edit
After Stannis Baratheon defeated Mance Rayder at the Wall in 300 AC he began to set his sights upon reclaiming the North and uniting them under his rule so he could challenge for the Iron Throne. Stannis initially set his sights upon reclaiming Deepwood Motte and some other holdings in order to win the support of the Northern Lords. Stannis was successful and even won the support of the Mountain clans who offered him additional soldiers.
Stannis would find himself marching towards Winterfell as a fierce winter began to take hold in the North. Stannis knew that Winterfell was the key to the North and that with it, even without a Stark he would be able to hopefully rally some support behind. Little did Stannis know, the North WOULD find itself a Stark, as the smuggler Davos Seaworth had been sent to Skagos to retrieve the young Rickon Stark.
Stannis Baratheon remained fortified in Winter Town for many days and nights, peering into the fire of the signal tower. The snow poured down hard and made for harsh days for his camp. His men, taking advantage of the nearby ice-lake, took to fishing it out for food. Roose Bolton deployed his two most contentious armies to meet Stannis - Hosteen Frey and the Manderlys. The Freys, mounted and plated, arrived in force on the other side of the icy pond. Seeing an opportunity, Hosteen leads a cavalry charge at the army of Stannis Baratheon but halfway through the pond, the ice suddenly gives out, leading to chaos. The ice, still fresh and fragile from the holes drilled by Stannis’ men earlier that day, proves unable to hold up the host and Hosteen Frey drowns under the weight of his horse awhile much of the Frey host sinks. The remainder that had managed to escape the ice prepared a retreat, only for the Manderlys to turn on them and then a hidden Umber force to ride out to sortie them.
Stannis continued his march and burned Theon Greyjoy to earn favour from R'hollor and to quell a blizzard which was impeding his march. The blizzard lifts within the day and by the next the snow began to melt leaving Stannis and his host to ride for Winterfell in preparation for the battle. Roose, having rode back to the Dreadfort with his wife Lady Walda, left his son Ramsay with a host to deal with the Baratheon. Due to food stores in Winterfell being horribly depleted, many of Ramsay’s men were already on edge.
Perhaps he should have been called Ramsay the Reckless, for he opened the gates of Winterfell and charged against the host of Stannis Baratheon which was in the process of setting up siege equipment. What would follow would be a fierce battle outside of Winterfell, with the Baratheons, Manderlys and Umbers narrowly claiming the victory.
Death of Stannis Baratheon Edit
Inside Winterfell from behind closed doors, tensions become high as arguments form between Stannis Baratheon and Wyman Manderly, particularly over the death of Davos Seaworth. Stannis decides to have Wyman imprisoned while he thoroughly investigate the rumors of his Hand's death. Tensions continue to rise and at least two assassination attempts are made on Stannis by Bolton men. Becoming impatient, Stannis writes to Roose Bolton demanding he broker peace and offering the wall for him and Ramsay. Shortly after sending the letter, Stannis is found dead with his throat cut open in bed.
Stannis’s men are quick to anger and blame Ramsay, who immediately denies accusations. Demanding he be put to the sword, the Lords within Winterfell decide to agree to this after Stannis’s men agree to release Wyman Manderly. Ramsay Snow is put to the torch, cackling like a madman and hurling insults at everyone. Within the same night, Roose’s reply arrives simply stating that he will not bend and to go ahead and kill the damn bastard.
The war falls to a standstill, as Wyman attempts to summon up the strength of the remaining Stark loyalists. Their efforts become validated at the news of Davos Seaworth’s return with Rickon Stark, having found him on the island of Skaagos. Learning the news of the death of his King and seeing the army disband with their King dead Davos goes into mourning, but marches for the Wall, with vows to retrieve Shireen as his last duty to King Stannis.
Rickon Stark is named Lord Paramount of the North, and Wyman is named his regent. Calling for Roose to be put to the sword, the army of the North sets out to rid themselves of Roose Bolton, once and for all.
Capturing the Dreadfort Edit
The men of the North marched without haste, making way for the Dreadfort. Roose Bolton had sealed himself away within the fort, having his own men defend it in full force. Roose was content to watch the Northman arrive in force, some even suggested that it was his intention to lose Winterfell, leaving the other Northerns bloody while the Dreadfort would be prepared for a siege in the same way that it had held out against armies in the past. His wife, Lady Walda Frey gave birth that morning ensuring that his legacy would continue following his victory
With all of the Northmen gathered, Roose knew that he had several options. He could stall them out, let them starve or meet the tired soldiers in battle. Roose knew that he couldn't outlast them forever in a siege, his food supplies were finite and his own sworn houses ignored his calls, suffering from losses of their own. His allies in the south had been undone by a Dragon and by themselves.
And so, Roose agreed to meet a diplomat.
A week passed while negotiations took place in the Dreadfort. Some men in the Northern host were become antsy, believing that the Lord of the Dreadfort would soon emerge wearing their diplomat's skin on his body.
As one probably could have predicted and as things have always worked in this world, things turned bloody.
Negotiations broke down in a torrent of blood, as Roose Bolton showed he wouldn't deal any longer with the diplomat. The Diplomat's head was placed upon a pike upon the Dreadfort's walls after the man suggested Roose surrender. Not another word would be heard from the Dreadfort since then, leaving only one option: The Sword.
The advantage was still in Roose's favour as the defender, but the sudden arrival of Jon Snow and several thousand wildlings changed all that. Shocked by new amount of forces that outnumbered his own, Roose realized that the Northerners would soon storm his walls. Fearing what would come of him if captured, Roose made a choice, a choice which would end this war.
Under the protection of night Roose Bolton fled the Dreadfort while the Northerners prepared their attack. He escaped alone and without informing everyone, fleeing the Dreadfort by way of the Northern road. The garrison in the Dreadfort would learn the next morning that their lord had abandoned them, and when the Northerners began to storm their walls, the Dreadfort fell into panic and quickly surrender, leaderless and unable to defend themselves after their Lord had abandoned them.
Hunting the Boltons Edit
Upon learning of Roose's flight, Mors Umber and Jon Snow would be the ones who lead men in the pursuit. They would pursue Roose over thick and thin over the next month, past the Northern Mountains and through the Northern snow to the point where they had him cornered just a few miles from the Gift.
But Roose suddenly made another choice like he did the night prior, and chose to ride to the Night's Watch to enlist, not wanting to turn himself over to the vengeful Northerners and hoping to have his life preserved until he could plot his return. Despite Mors want to press on, the Bolton's ploy worked, as Jon Snow whom still respected and understood the Night's Watch ordered the march back to the Dreadfort, leaving Roose to his devices and out of reach.
Jon and Mors returned just in time to hear Lord Regent Manderly proclaim victory. Discussions quickly turned to Roose Bolton's heir, the young babe born to Walda Frey. Wyman would famously declare that he would take Roose's son as 'ward' and hostage saying that he was half a Frey as well as Bolton and that "They took my son, now I'll take theirs."
Roose Bolton would end up murdered on the wall a few months later by a dagger in the dark, a dagger rumored to have come from his own Black Brothers. The line of the Flayer was left in shambles, only continued by a babe of a few months, held prisoner by a Merman as a taunt to his enemies.