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Winterhold (otherwise known as Winter Hold) is the former capital of Skyrim. At its peak, Winterhold was able to compete with the likes of Solitude. Despite its isolation from the rest of Skyrim, Winterhold remained wealthy and prosperous.
Winterhold is located in the coldest region of Skyrim. In 4E 201, Winterhold has been reduced to a small longhouse resting on the mountains, an inn, and a trader. Anything resembling the former capital has disappeared. Winterhold has only one road that continues to Fort Kastav and Windhelm.
Legends say that the great Arch-Mage Shalidor built the city of Winterhold from a whispering spell. In 1E 369, King Borgas, the High King of Skyrim and ruler of Winterhold, was murdered in Valenwood because of the infamous Wild Hunt. The failure to appoint Hanse as the successor of Borgas resulted in the War of Succession. In 1E 2804, a rebellion in Winterhold had occurred because of conscription quotas imposed by the Empire.
In 3E 399, The Eternal Champion had visited the city of Winterhold in the efforts of finding the Staff of Chaos. They visited the local Mages Guild and met with Thelen Kaarn, who asked the hero to travel to the Fortress of Ice to retrieve a missing tablet in return for the location of a piece of the Staff of Chaos. The hero retrieved the tablet and went on to Labyrinthian.
Before the Oblivion Crisis, a large population of Dunmer came to Winterhold to study at the College. Eventually, they were driven out of the city.
In 4E 122, Winterhold suffered from a tragic event known as the Great Collapse, which caused the majority of the city to be swallowed up by the sea. No one knows the reason for this, but the people of Winterhold blame the incident on the college.
During the Skyrim Civil War, Winterhold has garnered support from the Stormcloak Rebellion and Ulfric Stormcloak. The city has been reduced to only three standing buildings not including the College. The Jarl of Winterhold orders the Last Dragonborn to retrieve the Helm of Winterhold since it was taken. The Last Dragonborn also attends the College as a student and eventually becomes the Arch-Mage.