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Skingrad, the Gem of Old Colovia, is one of the oldest continual settlements within West Weald, with evidence of habitation going back to Elven settlements of the Methic Age. Sprawling over several rocky outcroppings and connected by bridges, the city is eminently defensible, and has expanded and contracted over its long history. Regardless, throughout the years the city has remained a center of creative activity, food, and culture. Its temperate climate and fertile soil makes it ideal for grapes and tomatoes, and its cheese-making is renowned throughout the continent.
Skingrad was without a doubt originally an Ayleid settlement, though no written records found so far confirm that. Excavations for new structures often reveal buried foundations, underground passages, and mosaic floors long hidden from the light, all with the High Elven style. Humans were also present, as evidenced by more humble dwellings and carvings, and were most likely Nedic people. As time passed [sic]
Following the Alessian Revolt of the Nedic peoples and the slow diaspora of the elves, Skingrad passed into the hands of human rulers. During this time Skingrad was established as one of the many petty kingdoms which owed their vassalage to the White-Gold Tower but remained independent. With the cities of Anvil, Chorrol, and Kvatch, they formed the nucleus of the Colovian Estates, and resisted much of influence [sic] of the rising Alessian Order.
Matters came to a head when the royal family of Skingrad was almost completely wiped out by plague, and the senior surviving member, Dorald Larich, an Alessian priest, ceded the kingdom to the First Empire. Another surviving prince, Rislav Larich of Kvatch, led a force against the city and overthrew and killed King Dorald. Emperor Gorius dispatched an army to Skingrad, but those forces were destroyed by Rislav's army, supported by his father-in-law, King Justinius of Kvatch. The defeat of the all-powerful imperial forces encouraged other city-states to rebel, and Colovia and the other western parts of empires fractured into smaller kingdoms, sometimes allied with each other, sometimes battling.
Skingrad maintained its status as an independent state for centuries but was eventually absorbed into the Reman Empire as the men of Tamriel united to repel the first Akaviri invasion. During the period of the Remans, Skingrad became more closely tied to Cyrodiil. The fourth Reman Emperor, Brazallus Dor, maintained a country estate nearby, and spent much of his rule engaged in feasts and other debaucheries, allowing his potentate to run the empire. This era established the city as a hub for culture, supported by the fine vineyards that had grown up around it. Emperor Dor is said to have died on his estate following a particularly intense set of debaucheries.
Skingrad became an ally of Duke Varen Aquilarios in his bid to overthrow the last of the Longhouse Emperors, Leovic. With Varen's ascendency to the throne, Skingrad rejoined the Empire as a vassal state, swearing allegiance to the Ruby Throne.
In the present-day, Skingrad is officially part of the Empire, but has not chosen to side with any particular alliance in the Three Banners War. They aggressively protect their neutrality and maintain several cohorts of the Imperial Legion to protect their borders. This aggressive neutrality has not kept the current count, Calantius, from launching his forces in an ill-considered assault on Reaper's March. Regardless, these actions have not dampened the cultured, independent spirit of the people of Skingrad, and it remains the jewel of West Weald.