Roose Bolton rode at the head of his column, leading his army through the narrow causeway of Moat Cailin. He had crossed the Neck and was now in the North. He sent his cavalry ahead to scout, gather news, and contact Ramsay. Their plan was to meet at Winterfell, and from there, they would intimidate the entire North, forcing every lord to swear allegiance to their new warden.
Five days later, Ramsay's army arrived. He had driven his mix of elite soldiers and peasant levies relentlessly, and they were the first to reach the winter town outside the castle walls.
The townspeople watched in terror as the army bearing the flayed man of the Dreadfort poured into their streets. Doors were barred and windows were shuttered. Families hid in their homes, peering through cracks in the wood with fearful eyes at the soldiers outside.
"Surround Winterfell!" Ramsay barked, ignoring the exhaustion of his men. "Don't let a single Stark escape!"
His first order upon arrival was to form a perimeter around the castle, trapping Sansa, Bran, and Rickon Stark inside. By capturing the last of the Starks, the Boltons could cement their control over the North.
In the winter town stood a small, fortified outpost belonging to House East. Its garrison of one hundred soldiers had closed the gates long before Ramsay's army arrived. The Bolton soldiers were not allowed to enter.
Several times, groups of Bolton men tried to storm the small castle, but they were driven back each time by the disciplined soldiers within, leaving dozens of dead and wounded behind. After their failed attempts, the Bolton soldiers gave up and turned their attention to looting the homes of the townspeople.
When Ramsay received the report that his men couldn't take the outpost and had lost dozens of soldiers in the process, he was furious. Escorted by a hundred cavalrymen, he rode to the small castle to see it for himself.
He stared up at the stone walls, which stood seven or eight meters high. He could see the soldiers of House East on the battlements, holding powerful-looking crossbows. The bodies of his own men littered the ground outside the gate. His face twisted into an ugly sneer, and his grey eyes glittered with a sinister light.
After a moment of consideration, Ramsay decided against ordering another attack. He knew his soldiers were exhausted from the forced march. Robbing the helpless townspeople was one thing, but storming a fortified position would be costly. He would likely lose hundreds more men.
Ramsay only had about two thousand men in total. He needed them to surround and capture Winterfell. He couldn't afford to waste them on this small outpost. He had heard the castle was a trading post for House East's unique goods and was likely filled with wealth. But money could wait. His main target was Winterfell and the Stark orphans. Once the castle was taken and his father's army arrived, the riches in this small fort would be his for the taking anyway.
Having made up his mind, Ramsay waved his hand. He left a small contingent of soldiers to keep watch on the outpost and led the rest of his army to make camp outside Winterfell's main gates.
Inside the small castle, the defending soldiers breathed a collective sigh of relief as they watched Ramsay and his army depart. The garrison was composed of one hundred spearmen, not yet equipped with flintlocks. While they were better trained than Ramsay's men, they were severely outnumbered. If Ramsay had ordered a full-scale assault, they would not have been able to hold out for long.
Fortunately, before the Bolton army had arrived, they had sent a rider to their logging camp ten kilometers away. The camp received the news and immediately sent another messenger to find Lord Jason, who was approaching with the main army. At the same time, the workers at the camp were ordered to stop cutting trees and fall back behind their own walls, fearing an attack from the Dreadfort soldiers.
The logging camp itself had a garrison of a thousand soldiers. But with news that Roose Bolton was bringing tens of thousands of men from the south, they knew they couldn't risk sending support to their comrades in the winter town. They could only secure their own position and wait.
Inside Winterfell, panic had taken hold. Young Sansa knew only how to be a lady. Bran was still a boy, and little Rickon was so frightened he could only cling to his sister and cry.
Ser Rodrik Cassel, the master-at-arms, was still recovering from old wounds, but he pushed through the pain to organize the defense with Maester Luwin. All they had were the three hundred soldiers left in the castle. These men were the last of Winterfell's guard, recalled to the castle for protection after Theon Greyjoy's raid more than a month ago.
Ser Rodrik and Maester Luwin climbed the battlements and looked out at the two thousand Dreadfort soldiers setting up their siege lines. Their faces were grim.
"Damn Roose Bolton," Ser Rodrik growled, slamming his fist on the stone parapet. "That treacherous, backstabbing scum!" The old knight's white beard trembled with rage as he stared at the flayed-man banners below.
A thin layer of sweat beaded on Maester Luwin's brow. Ever since he learned that Lord Robb and Lady Catelyn had been murdered at the wedding, the old maester had been overcome with sorrow. The wrinkles on his face seemed to deepen with every passing day. He had served House Stark for more than forty years and had come to see them as his own family. Watching them die one by one was heartbreaking.
But he knew he had to remain strong. For the sake of the children, he had to help Bran claim his title as Lord of Winterfell and continue the Stark line. It was the only way to honor the memory of Lord Eddard and the others.
No one could have imagined such a disastrous turn of events. Lord Robb had seemed invincible, winning victory after victory and becoming King in the North. It felt as though House Stark was on the verge of restoring its ancient glory. Then, in an instant, everything was lost. Lord Robb and the northern lords were dead. Roose Bolton had betrayed them all.
Now, Winterfell was besieged. If the castle fell, Lady Sansa, Lord Bran, and little Rickon would be captured, and their fate would be tragic beyond imagining.
What can we do? Luwin thought, his heart filled with despair.
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