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Bitterbridge, once known as Stonebridge, is the seat of House Caswell in the Reach. This modest yet strategically important stronghold lies where the river Mander meets the Roseroad, serving as a crucial crossing point and a hub for travelers and traders alike.

The town of Bitterbridge derives its name from an ancient stone bridge that spans the Mander. This bridge, vital for its strategic position, has witnessed countless events and the passage of many armies and merchants. The castle itself is small, constructed of stone and timber, reflecting the pragmatic architecture of the region. Though the keep is not particularly tall, the surrounding flatlands enhance its apparent height, making it a prominent feature in the otherwise low-lying landscape.

Bitterbridge's importance extends beyond its physical structure; it serves as a critical junction in the Reach. The convergence of the Roseroad and the Mander river at this point facilitates the flow of goods and people, enhancing the economic vitality of the region. This accessibility, however, has also rendered Bitterbridge vulnerable in times of conflict.

In recent history, Bitterbridge endured significant destruction. The Hogs Head, a disreputable inn known for its rowdy clientele, was the first building to be destroyed during the sack of Bitterbridge. This violent event marked a significant loss for the town, as the Hogs Head was not just an inn but a social hub for many of its residents. The town's sept also suffered during these attacks, falling victim to the devastating power of dragonflame. The loss of the sept, a place of worship and communal gathering, further underscored the tragic impact of the conflict on Bitterbridge.

Despite these adversities, House Caswell continues to hold Bitterbridge, maintaining its role as a key player in the intricate web of alliances and enmities that define the Reach. The resilience of Bitterbridge and its people remains a testament to their enduring spirit and the strategic significance of this humble yet pivotal location.