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Oldtown, located on Whispering Sound in the Reach’s southwestern coast, is one of Westeros’s most storied and affluent cities. Built around the iconic Hightower on Battle Isle, it serves as the seat of House Hightower and houses the famed Citadel, home to the order of maesters and their Conclave, as well as the Starry Sept, once the heart of the Faith of the Seven.

The city, known for its cobbled stone streets, labyrinthine alleys, markets, and walled fortifications, is rich in both history and wealth. Streets like the Thieves Market and Ragpicker's Wynd wind through Oldtown, lined with fragrant flora, including peaches, pomegranates, and nightshade. Oldtown is also dotted with bridges, many of stone, which cross the Honeywine River that flows through the city’s heart, and smaller islands like the Quill and Tankard inn add to its unique charm. The Starry Sept, along with several other septs, honors the Seven and lies within the city, with temples for foreign faiths near the bustling harbor.

The Hightower, a towering lighthouse of unprecedented height, guards Oldtown’s port and serves as a beacon for incoming ships from across the world. This mighty structure, taller even than the Wall, stands on Battle Isle, built atop an ancient black stone foundation, and has survived centuries of attacks.

Oldtown has a rich trade economy, being Westeros’s wealthiest city and second only to King’s Landing in population. Its bustling port welcomes trading ships from across the world, including the Summer Isles and Free Cities. House Hightower, originally kings but later vassals of House Gardener and now the Tyrells, rules the city and owns the Bank of Oldtown.

Historically, Oldtown’s origins date back to the Dawn Age, when First Men settled at the Honeywine's mouth, likely as a trading post. During the Age of Heroes, pirates threatened Oldtown’s burgeoning wealth. Over time, the city fortified itself with walls built by King Otho II Hightower. In the centuries that followed, Oldtown joined the Kingdom of the Reach when the Hightowers allied with House Gardener, creating the foundation for its enduring influence.

Today, Oldtown remains the center of learning, culture, and trade in the Seven Kingdoms, where knowledge and wealth converge at the towering Hightower and the grand halls of the Citadel.