Oldtown

Oldtown is one of the largest and oldest cities in Westeros, built by the First Men before the Andal invasion. The city was constructed around the seat of House Hightower, called the Hightower, located in the centre of the city. Oldtown is further home to the Citadel, and houses the Starry Sept, formerly the seat of the High Septon of the Faith of the Seven before Aegon’s Conquest.

Oldtown is located at the mouth of the Honeywine in the southwestern side of the Reach. It is a port city, and serves as the realm's second most important harbour. Trading ships from all the world, including other Westerosi places, the nine Free Cities, the Summer Isles, and more, are known to call upon Oldtown's port.

To the north of the city, the seats Honeyholt and Brightwater Keep can be found. To the east lies Uplands, and to the west Blackcrown and Three Towers. To enter the port of Oldtown from the Sunset Sea, one first needs to enter the Whispering Sound. The Roseroad travels from Oldtown to Highgarden, from where it continues on to King's Landing.

The city is a labyrinth of wynds, crisscrossing alleys, narrow crookback streets, and markets. These include the Thieves' Market and Ragpicker's Wynd. Oldtown is built in stone, with all its streets cobbled, which can make them wet and slippery on a damp day. Most bridges are made of stone as well, although some wooden bridges can be found as well. The city itself is surrounded by massive, thick, high stone walls. The river road winds along beside the Honeywine through the heart of the city. West of the river, the Guildhalls line the river bank. In the undercity of Oldtown, rat pits and black brothels are located.

Oldtown is also home to three great monuments. First of these is the Citadel, located upriver on both sides of the Honeywine. Here, boys and men can gather from all over Westeros to learn and study, and to forge a maester's chain. The Citadel is considered to be the greatest seat of knowledge in the world.

The second monument is the Starry Sept of the Faith of the Seven, located downriver. It was raised on the command of Lord Triston Hightower and became the seat of the High Septons for a thousand years, which made Oldtown the unquestioned center of the Faith for entire Westeros. Only following the construction of the Great Sept of Baelor in King's Landing during the second half of the second century after Aegon's Conquest, did the Starry Sept lose its status. Besides the Starry Sept, at least seven more septs honoring the Seven, built on the command of Lord Damon Hightower, can be found in Oldtown or on the city's lands. These include the Sailor's Sept down by the harbor, the Lord's Sept, and the Seven Shrines in their gardens across the Honeywine. Oldtown is also home to a motherhouse. Down by the wharves, temples that cater to foreigners can be found, such as Summer Islanders and red priests of the Lord of Light.

The third monument is the mighty Hightower, a massive stepped lighthouse located on Battle Isle, where the Honeywine widens into Whispering Sound. The Hightower has a great beacon on top, which shows ships the way to port. It is the tallest tower in the world, higher even than the seven-hundred-foot Wall.

The Second War of Conquest
After making a feint toward the Arbor, Euron Greyjoy sacked Oldtown and its surrounding villages. The unexpected arrival of the combined forces of the Reach under Lord Randyll Tarly and Dorne under Lord Franklyn Fowler crushed the Ironborn in an initial engagement and them Ironborn to retreat to their ships. Cut off from reinforcements and caught between an army on land, the Redwyne fleet on the sea, and Daenerys Targaryen's dragons in the air, the Crow's Eye met his end.

The Summer Sickness
In the year 345 A.C., ships from the Summer Isles brought the Summer Sickness into Oldtown, which quickly spread throughout the Reach. Similar outbreaks happened in other port cities throughout Westeros, even claiming the life of King Rhaegar I Targaryen. The horrific death toll in Oldtown led to many people beseeching the gods for deliverance, and this groundswell of pious devotion was certainly a factor in the coming schism.

The Southern Schism
In 346 A.C., a significant number of the Most Devout fled King's Landing and the excesses of the Mummer Septon. Their arrival in Oldtown was the beginning of what became known as the Southern Schism. For three years, the realm was divided in their religious allegiances between rival High Septons in King's Landing and Oldtown until King Aenar stepped in and resolved the matter. Though there have not been any riots between followers of the Baelorian and Starry Rites in decades, there are still rival schools of thought and occasional simmering tensions.

The Great Famine
The Great Famine struck Oldtown hard. The unusually cold weather and shortage of labor to gather the harvest meant that a region that ordinarily exports food was unable to feed itself. Many starving peasants came from the countryside to Oldtown, overcrowding the city and exacerbating the food shortages. The Starry Septon preached that the gods had sent the Famine as a punishment for their sins and made a Walk of Penance through the streets of the city on behalf of the populace.

The Scarlet Winter
Though Oldtown itself did not remain frozen for the whole of the winter, it did freeze over for months at a time during the worst years of the season. Promises of Hightower wealth brought merchants, desperate or bold, regardless; the frozen harbours of Lannisport offered little hope for other markets upon the western coast.