Although it’s origins are largely lost to history, Old Town has stood for thousands
of years known as the richest and oldest of the Westerosi cities.
Many believe it was originally constructed as a port for ancient powers that wished to
trade with the elder races of Westeros, and later with the First Men who migrated into
the continent.
Over the years several well known structures were built in the city such as the Citadel
a group of buildings that are home to the Maesters of Westeros, scholars who value knowledge
and act as advisors to the rulers of the continent.
During the Age of Heroes, the building that later became the Ravenry of the Citadel was
a pirate stronghold that robbed passing ships.
There is also the Starry Sept, which was the center of the Faith of the Seven for a thousand
years, until replaced by the Great Sept of Baelor in King’s landing.
But the structure most often associated with the city is the Hightower on battle isle,
known as the tallest building in the continent, surpassing even the 700 foot wall in the north.
The Hightower was built atop a blackstone foundation, believed to have been constructed
before the arrival of the first men.
While some claim it must have been of Valyrian origin, since they were known to build with
fused black stone.
The look and design of the structure and time period in which it was made, suggest it was
built by others such as the mysterious Mazemakers of Lorath, or the Deep Ones rumoured to have
built the Seastone chair in the Iron Islands.
When House Hightower took control of the black stone foundation on battle isle, they built
a wooden tower on top to act as a lighthouse but under Uthor of the Hightower, they built
a stone tower 200 feet high, supposedly designed by bran the builder.
The prosperous city of Old Town grew around the Hightower, and came to represent a valueable
target for raiders, seeing the city sacked by Samwell the Starfire, Qhored the Cruel,
and Gyles the Woe, all within a century.
Due to this devastation of these attacks, three quarters of the city's population were
sold into slavery.
However the Hightower was never conquered, and so House Hightower then oversaw a massive
project to build protective stone walls around the city, greatly increasing its defensive
capabilities.
As the Kingdom of the reach expanded under the Gardener Kings of Highgarden, the Hightowers
chose to join them voluntarily through a marriage alliance, giving up their claim as petty kings,
to become the most powerful vassals of the realm.
The Hightowers often valued peaceful negotiation over war, like during the Andal migration
when the leader of their house married an Andal Princess to avoid conflict.
Similiarly, when House Targaryen invaded and conquered most of the continent, the High
Septon convinced Lord Manfred Hightower to bend the knee.
Allowing Aegon to peacefully enter the city where he was crowned king of westeros by the
faith of the seven.
Many though Aegon would then choose Old Town as his capital, until he decided to build
a new city around the Aegonfort, later known as King’s Landing.
2 centuries later in 209 AC, Old Town suffered greatly as the Great Spring sickness spread
throughout the continent.
Although King’s Landing saw the worst of the epidemic, Old Town was not far behind,
then suffering another tragedy a generation later, when the Grey Plague wiped out half
the city.
In order to prevent the disease from spreading, Lord Quenton Hightower locked them down, shut
the gates and burning the ships in the harbour, killing anyone who tried to leave.
Although he succeeded in preventing a further outbreak, his harsh actions made him hated
by the small folk who later attack and killed Lord Quenton and his son.
Late into the War of the Five Kings, with the Arbor Fleet being used in the Lannister
siege of Dragonstone, the Ironborn conquered the Shield Islands of the reach with some
of their people even attempting to attack Old Town, while others preyed on ships sailing
into its harbor.