Wayrest is one of the most glorious cities of western Tamriel: sparkling in her contemporary beauty, lustrous by her past. She is prized above all cities in High Rock -- no other city has contributed, and continues to contribute so much to the culture of the Bretons. The spirits of her genius children continue to haunt the streets; you can see them in the gabled roofs, grand boulevards, aromatic marketplaces. The people of Wayrest have an appreciation of their past, but are not obsessed by it, as the people of Daggerfall seem to be. One feels that one is in a modern city when one visits Wayrest, but there is a magic in the air that could only come from thirty-two centuries of civilization.
It is difficult for historians to declare a certain date for the foundation of Wayrest. A settlement of some variety had been existence where the Bjoulsae River feeds the Iliac Bay possibly since the 800th year of the First Era. The traders and fishermen of Wayrest were surrounded by hostile parties: the orc capitol Orsinium had grown like a poison weed to the north, and the Akaviri pirates and raiders crowded the islands to the west. There is no mystery to Wayrest's name. After the fighting most travellers had to endure passing through the eastern end of the Iliac Bay, the little fishing village on the Bjoulsae was a welcome rest.
Nowhere in the much vaunted censuses of the Skyrim Occupation is Wayrest mentioned. In the Annals of Daggerfall, King Joile's letter to Gaiden Shinji of the Order of Diagna contains the following reference: "The orcs have been much plaguing the Wayresters and impeding traffic to the heart of the land." The date given for the letter was 1E 948.
Wayrest only truly bloomed after the razing of Orsinium in 1E 980. The hard-working traders and merchants were instrumental in forming the Masconian Trade Way and thus reducing the pirate activity on the Bay. At this time, Wayrest occupied both banks of the Bjoulsae. A successful mercantile family, the Gardners, built a walled palace on the High Rock side of the river and, over time, allowed banks and other businesses within its walls. It was a Gardner, Farangel, who was proclaimed king when Wayrest accepted ambassadors from the Camorian Empire, and was granted the right to call itself a kingdom in the 1100th year of the 1st Era.
Although Wayrest became a kingdom under the command of one family, the merchants continued to wield incredible power. Many economists have alleged that Wayrest's eternal wealth, despite all her hardships, comes from this rare relationship between the merchants and the crown. The Gardner Dynasty fell, followed by the Cumberland Dynasty, which was followed by the Horley Dynasty, and finally, in the Third Era, the Septim Dynasty. No citizen of another kingdom of comparable age can, with one hand, name all the families who have ever ruled. Never has a king of Wayrest been deposed by revolution or assassination. Except for those of the Septim family, every king of Wayrest can trace his line back to a merchant prince of Wayrest. The merchants and king respect one another, and this relationship strengthens both.
One need only walk down the great boulevard of Wayrest to see physical proof of this unique alliance. Going north to south, Wayrest Boulevard suddenly divides, one half going west and the other going east. Both halfs end in identical squares: one at Castle Wayrest, the original palace of Aphren Gardner, and the other at Cumberland Square, where the oldest and wealthiest marketplace in Wayrest. The message here is clear: the king and the merchants are joined and equal.
Wayrest has survived blights, droughts, plagues, piracy, invasions, and war with good humor and practicality. In 1E 2702, the entire population of the city was forced to move into the walled estate of the Gardners as protection against the pirates, Akaviri raiders, and Thrassian plague. A less resourceful community would have withered, but the Wayresters have survived to enrich Tamriel generation after generation.