Freeport is a city unlike any other. Isolated from the mainland by an ocean, just about anything goes in Freeport. Flintlock weapons are commonplace, although that wasn't always the case. Many a pirate has his origins in Freeport, including Baldric, Wendron Krubach, and more. Freeport's ruled by a Captains' Council and a Sea Lord, but the Sea Lord position is inherited just like a king.

Much of Freeport's woes involve choosing a new Sea Lord after the Player Characters killed Milton Drac. There are several candidates for the position of the next Sea Lord, including Emric and, despite straining all credibility, Captain Drak Scarbelly.

In addition to the question of who will be the next Sea Lord, Freeport has two other problems: the Brotherhood of the Yellow Sign and an underground population of Valossan Ssanu. It appears that the ssanu once ruled the island nation of Valossa, before an insane deity destroyed the entire city. Eventually, humans took over, but the ssanu went underground, plotting their return.

There are several theories as to who the insane deity was that destroyed the Valossan civilization. Elorii believe it to be Umor. Others call it the Unspeakable One. Then there's the Brotherhood of the Yellow Sign, who calls it the King in Yellow.

The Brotherhood of the Yellow Sign has recently found a revival in both humans and ssanu in Freeport. This brotherhood seeks to bring back the King in Yellow, thereby turning all of Freeport completely mad before it is destroyed in one big, glorious orgy of violence. Milton Drac, a secret member of the Brotherhood, nearly achieved this goal by building Milton's Folly, a lighthouse that projected the Yellow Sign into the skys over Freeport. Fortunately, his attempt failed...for the most part.

Some Freeport citizens DID see the Yellow Sign, specifically, the entertainers who were facing the lighthouse as the time the Sign was activated. One of these was an elorii disguised as a human known as Cael Greybeard. He took the insane knowledge of summoning King in Yellow back with him to Moratavia and nearly shifted the entire territory into Carcosa.

Freeport's woes never end. As a generally neutral city, it is courted during wars between other nations to become privateers, hiring out its pirates to strike against the enemies. This causes something of a bidding war, but Freeport must choose carefully lest it pick the losing side.