Oldtown is, as its name might suggest, the oldest city in Westeros. It was originally built by the FIrst Men and might not have made it to the current age had its leaders chosen to defy the Andal invaders. Instead, the city opened its gates to them – a tactic that would just as well when Aegon the Conqueror moved south with his dragons. The city was also the largest on the continent prior to Aegon’s Conquest, but the establishment of the Iron Throne at King’s Landing resulted in it surpassing Oldtown in size. Oldtown is constructed entirely of stone, and every street – be it a primary throughfare or simply a shaded alley – has been built with cobblestones.
The city is located around the mouth of the Honeywine River where it empties into Whispering Sound. This fact alone is enough to make Oldtown one of the most important places in Westeros, both to The Reach and the continent as a whole. It is Westeros’ preferred trading port, with ships from the Summer Isles and the Free Cities weighing anchor there.
Oldtown is a preferred port because of the ease by which ships can navigate into the sounds. The primary reason for this is the Hightower, the tallest structure in all of Westeros. The Hightower is a gigantic lighthouse that rises from the bluffs of Battle Island in the center of the city. The tower rises in a series of setbacks some eight hundred feet up to its beacon, which can be seen for miles in all directions. The rest of Oldtown was constructed around The Hightower, and it is said the city’s citizens can tell what time of day it is based on where the building’s shadow falls. In addition to its job guiding ships into the harbor, the lighthouse also serves as the seat for House Hightower. The Hightowers had been kings in their own right before bending the knee to the Gardeners. House Hightower rules Oldtown, and so it remains one of the more important houses within The Reach.
The city follows the Honeywine, with the various guildhalls lining the west bank. Further up the river is The Citadel, the center of the maesters, those rare individuals who have chosen a life of service for the greater good of the kingdom. The Citadel lies on both sides of the Honeywine, with numerous stone bridges connecting the two halves. Flanking the main gate are a mated pair of green marble sphinxes, and beyond them is the Scribe’s Hearth, where acolytes fulfil most of the mundane tasks required by Oldtown’s citizenry. This is as far as most visitors will ever enter into the maesters’ realm. The maesters are led by a group of Archmaesters known as the Conclave, who make decisions such as which members of their order should be assigned to certain houses or castles, who amongst the acolytes or maesters is ready to be promoted to the next rank, and so forth.
Many of the Citadel’s novices and acolytes make a second home of the Quill and Tankard, an inn and brothel situated on a terraced island on the Honeywine. Patrons from every rung of the social ladder visit the Quill and Tankard to quench their thirsts for drink and baser pleasures. The timber structure is some six hundred years old, and though its upper stories now lean somewhat precipitously to the south, it has never closed its doors during that time. Many of the inn’s patrons prefer to take their beverages out of doors in any event since there is an abundance of green lawns on which they can take their rest.
Before Aegon’s conquest, Oldtown was the spiritual center of The Faith in Westeros, and the Starry Sept served as the seat for High Septons for a thousand years. When Aegon settled in King’s Landing, The Faith followed him, and Westeros’ primary religion is now governed from the Great Sept of Baelor. Yet, the Starry Sept remains an impressive sight, standing out from the surrounding structures because of the black marble used in its construction. There are a number of other septs in the city, including the Lord’s Sept, the Seven Shrines near the Quill and Tankard, and the Sailor’s Sept by the harbor. The city recognizes the need of the world’s other faiths, and sailors from trading vessels do not have to travel far from their ships in order to find a temple to their gods. Among the temples on the wharf is a modest one to R’hllor, the Lord of Light.