Roose Bolton states that Brandon the Builder, founder of House Stark, raised Winterfell with giants over eight thousand years ago, or so nursemaids tell all the children of The North. The children nod, wide-eyed, unaware of the lesson enforced on them; that if even giants obeyed a Stark, so too should they.
But like every other castle, Winterfell was built in pieces over thousands of years. The First Men settled there because of the hot springs that bubble through the ground. The water and the heat helped them survive the northern winters, and they built defences to keep it for themselves. Nobody raised the castle all at once. Bolton speculates that probably nobody meant to raise a castle at all.
In those days, the Starks were not the greatest house in the North, and Winterfell was not the greatest castle. Barrowton was the oldest, dating to the First King, and the Starks fought the Barrow Kings for a thousand years. Greywater Watch was, like the crannogmen themsleves, the strangest. Only marriage subdued its Marsh Kings.
But the greatest rival to Winterfell was always the Dreadfort, home to the Red Kings of House Bolton. If tales can be believed, they fought from the Long Night until the Andals came. It was because of the Boltons that Winterfell raised its first walls. When they took and burned the castle anyway, Winterfell built more keeps, more walls, more guard towers. They expanded the granaries and larders to survive the Boltons' sieges. They tended the godswood to win favor with the Old Gods against the Boltons.
As the castle grew, more farmers and villagers flocked every winter from across the North to huddle under its walls, raising its winter town. In the spring these villagers would find themselves marching in the Stark armies to fight against the Boltons. The greatness of Winterfell is as much the doing of the Boltons as it is the Starks.
But in the end neither its strong walls nor its tall keeps and iron gates could save Winterfell. At its height it could have lasted a year under heavy siege, but a handful of ironborn seized it in the night while its lord, the King in the North, was playing in the south. Roose's dagger ended his reign and now House Bolton holds the castle of their ancient enemies. The direwolf no longer flies from the battlements above Roose, nor guards the doors and cornaces of Winterfell against him. Below him miles of long dead Starks fade into darkness and obscurity, until even their faces are lost. Some northerners whisper that they wait for the day their house will rise again. He concludes by stating that they will wait forever.
- King Brandon Stark, the "Builder" (mentioned)
- First King (mentioned)
- King Robb Stark (indirectly mentioned)
- The North
- Barrowton (mentioned)
- Greywater Watch (mentioned)
- The Dreadfort (mentioned)
- The Long Night
- Andal Invasion (mentioned)
- War of the Five Kings