The First Battle of Winterwind Crag was a battle between invading Scourge forces and the defenders of Winterwind Crag. The battle was an early action in the Third War, but it enabled the Scourge to gain a stronghold in Alterac.
After the Roadwarden of Winterwind Crag was killed by Syndicate attackers, the traditional heirs to his position began bickering amongst themselves as to who should become the new roadwarden. Unable to settle matters, they instead chose to dive up the hereditary weapons that the past Roadwardens had used - collectively known as the Roadwarden's Arms - until they could make a decision over who would become the keep's new leader.
This situation did not sit well with Vidruand, the youngest of the three. Realizing that he had little chance of inheriting the position, he sought other ways to claim the keep for his own. He fell in with the Cult of the Damned, lured by their promises of power and immortality, willingly joining their number. Through them, he felt that he had found his path to power.
Vidurand lead a force of undead Scourge (Mainly Ghouls, but with a few animated Skeletons and Zombies as well) accompanied by a group of Necromancers from the Cult in an attack on the keep. Using his knowledge of the keep to their advantage, the cult were able to slip by the keep's defenders while Vidurand occupied them.
For his part, Vidurand called a meeting, claiming that he had reached a decision about his inheritance. This was in fact a ruse designed to draw his siblings and the majority of the keep's defenders into a single location. When the meeting started, Vidurand stated that he was going to claim sole control of the Keep, and that his siblings could either join him or die.
At that point, the concealed Necromancers rushed the main meeting hall, while the Undead forces assaulted the keep's defenders who were outside. Easily overcoming the initial defenses, the Undead swarmed through the keep, joining up with their masters. Very soon, every living being in the keep, save for those allied with the Scourge, were slain by the undead or their masters.
The fall of the keep gave the Scourge forces greater access to the Alterac Mountains, an asset that would allow them to march on Stranbahd as a part of Arthas and Kel'thazaud's greater plan. It also prevented the settlements to the south from having any advance warning of the forthcoming undead assault.
As a reward for his service (which included the slaying of his entire family), Vidurand was given control of the keep by the Scourge. Later, in the aftermath of the third war, he would be promoted to a Death Knight.
For the duration of the third war, the keep would be garrisoned by the Scourge. However, with the civil war and the emergence of the Forsaken, much of its forces would be withdrawn and instead redeployed to face the Horde forces at the Bulwark, or against the Argent Dawn at Chillwind Camp. Since then, the keep has remained largely uninhabited, and has fallen somewhat into disrepair.