Duskendale

Long before the Andals crossed the Narrow Sea, Duskendale already had rulers of its own: House Darklyn, a line descended from the First Men, had built the town and reigned over the coast as its own kings.

That small kingdom eventually dissolved into larger ones. Benedict II Justman, King of the Trident, folded the town into his realm during a long reign, together with Rosby and the mouth of the Blackwater. Later, Duskendale and Maidenpool answered instead to the Storm Kings.

A merchant named Addam also hailed from its streets; he sailed as far as eastern Essos and wrote down what he found there.

When the War of Conquest broke out, Duskendale was the wealthiest Westerosi harbor on the Narrow Sea, fattened by the trade flowing into its bay; before that, Halleck Hoare, King of the Isles and the Rivers, had already claimed it and Rosby for his own realm.

Lord Darklyn joined Lord Mooton in standing against Aegon Targaryen's forces, and both died in the fighting. It was Darklyn's son who finally surrendered the town. Visenya Targaryen forbade any sack, though she kept its riches for herself, and Duskendale became part of the newly formed Crownlands.

During the Dance of the Dragons, Ser Criston Cole struck Duskendale by surprise, punishing Lord Rosby for backing Princess Rhaenyra Targaryen. The ships in the harbor burned, and Lord Darklyn lost his head.

Some time later, when Rhaenyra fled King's Landing for Dragonstone, it was Duskendale that took her in, and only because Ser Harrold Darke spoke for her at the gates. There she sold off her crown to raise money before sailing on again, this time aboard the Violande.

As King's Landing grew, trade on the Narrow Sea drifted away from Duskendale and Maidenpool toward the capital, and the port's old splendor began to fade. Lord Denys Darklyn tried to halt the decline by seeking a charter for his town like the one held by Dorne, with lower harbor duties that might let it compete again.

The refusal sparked the Defiance of Duskendale: the Darklyns held King Aerys II Targaryen captive in the town for six months. Only once Ser Barristan Selmy managed to rescue him did the crown answer in kind, wiping out House Darklyn; the castle, lands and revenues of the town then passed to House Rykker.

Under Rykker rule, Duskendale hosted a tourney in 294 AC that Ser Balman Byrch would later claim to have distinguished himself in.

After taking Darry, Ser Helman Tallhart was ordered by Lord Roose Bolton to join forces with Ser Robett Glover and sack the town of Duskendale.

The venture went badly: Lord Randyll Tarly's troops defeated them outside the town, and Tarly held the region under his command from then on.

Later, Brienne of Tarth passed through Duskendale while searching for Sansa Stark, and found no trace of her there.