According to legend
Bran the Builder laid the first stone of Winterfell
over eight thousand years ago
However, Bran the Builder
is held to have raised every major stronghold and structure in Westeros
from storm's End to the Wall
and the truthfulness of this is hard to determine

Winterfell
has served as the stronghold of the
Kings in the North for most of recorded history

When Aegon the Conqueror invaded Westeros,
King Torrhen Stark bent the knee
when he saw the strength the Targaryens commanded,
and the Starks were retained as
the Warden of the North and ruling Lords of the North

During the War of the Five Kings,
Winterfell was captured in a surprise attack launched
by Theon Greyjoy
He successfully held the castle for several weeks,
but refused to relinquish it even though he lacked the manpower
to successfully hold it indefinitely against the Stark bannermen

Ramsay Bolton unexpectedly turned on his fellow northmen
and Theon welcomed him as an ally,
but was betrayed once more
Bolton razed the castle complex and took Theon prisoner...