Men have fished and traded at the mouth of the Honeywine since the Dawn Age, and Oldtown's own runic records — the oldest the First Men left behind — confirm a settlement here long before the Andals ever crossed the narrow sea. The city took its walls and much of its name from House Hightower, who built the tower that lights Whispering Sound and have ruled from Battle Isle ever since, first as a power the Andals had to reckon with and, in time, as loyal and formidably wealthy bannermen of the Reach.
In the first year after the Conquest, Oldtown opened its gates to Aegon without a fight — the sole great city to do so — and by long tradition the count of years the Seven Kingdoms still keeps began on that day. The city has since built its reputation on institutions rather than armies: the Citadel of the maesters, the Starry Sept that once seated the High Septon of the Faith, and a harbor busy enough that even King's Landing, for most of the realm's history, could not quite outgrow it.