With a rich bounty filling the seas, and dense forests lining the shores, it wasn’t long before the early inhabitants of Arrea’s eastern regions took to the construction of boats. Early vessels were little more than rafts, but as these early people’s confidence grew, it wasn’t long before small sailing vessels dotted the coast around the peninsula we now know as Lifeswallower. As humans are wont to do, these early mariners explored their world. As brave souls ventured east toward the rising sun, the natural geography of the region made exploration in small, moderately seaworthy vessels relatively easy. Situated like stepping stones in a small pond, the isles lining the continent to the east were, one at a time, discovered and explored in detail. The burgeoning science of cartography permitted the relative position of these islands to be recorded, while sages of the era developed the rudiments of astronomical navigation. In fewer than 100 years, the races of eastern Arrea were seafaring. 

As one would expect, men of ill intent soon exploited the benefits conferred to civilization by sea travel. Those seeking freedom, adventure, and potential riches were attracted to the vocation of pirate. Just as bandits on land generally inhabit a hidden lair to avoid the reach of law enforcement, so it was with pirates. Difficult-to-navigate inlets and coves curtained by barrier reefs offered a safe haven for those seeking to avoid detection by sea going lawmen. One such location can be found on the southern tip of the island Coventry. First recorded some 15 years after written maritime records began being kept in the city of Alranda (year 1 M.E. – Maritime Era), Coventry initially saw very little ship traffic. This was in large part due to the imposing barrier reef that encircles the island. This reef claimed so many vessels during the early period of Arrea’s seafaring history that the isle quickly gained a reputation as a sailors’ graveyard. 

Eventually, though, capable captains did utilize Coventry’s dangerous harbors. The isle’s indigenous gnomes record regular visits from human sailors around year 25 M.E. The meticulously kept records of the gnomes reveal that all of these early visitors to Coventry were pirates. There was simply no good reason for normal trade vessels to venture that far to the east. Because of the island’s bad reputation, these pirates enjoyed total freedom while within Coventry’s barrier reef. Small skirmishes no doubt flared up between rival pirate factions, but soon the roving sea bandits learned to cooperate. As the Pirate’s Code developed and they learned to work in each other’s best interest, Coventry soon grew into a safe haven for pirates and other seafaring rogues. A small village cropped up on the island’s southern tip, and the location became a preferred location for extended shore stays. This state of affairs remained essentially unchanged until 212 M.E., when the pirate captain Roderick Van Nigh declared himself the village’s first king. He christened the “city” Freeport and began collecting taxes.

Boomtown

The gnomes of Coventry record the murder of Roderick Van Nigh on the 2^nd of Mistbringer, 213 M.E. Roderick’s body was dumped unceremoniously in Mandrake Swamp, and, after less than a year, Freeport’s first human government evaporated. The village gradually grew into a town, and after another 60 years, attracted its next government.  Captain Frederick Hearns and his crew of over 100 sailors (sailing a fleet of 6 pirate vessels) were officially declared rulers of Freeport in 284 M.E. Hearns, unlike Van Nigh, was both feared and respected by his fellows. Instead of installing himself as a ruler and demanding tribute, Hearns’ authority over the town grew naturally from his leadership role within a very successful thieving operation. As Hearns’ pirating grew more and more lucrative, he soon found himself in charge of several vessels. Where one ship may need frequent repair and docking for provisions, a small fleet is essentially in constant need of some sort of service. Hearns was not only a sailor and a thief, but also possessed a keen mind for business. His crew soon consisted of a full time maintenance staff that never stepped foot off of dry land. Additionally, he kept a small group of rogues under his command that lived within Freeport and attended to all of Hearns’ vessels’ supply needs. It wasn’t long before the smart old captain realized that the logistical system he had set up for his own operations could be sold as a service to other, smaller operations. Captain Hearns quickly ascended to a position of near royalty status among the pirates of the region. Hearns used this position of wealth and authority to turn Freeport’s pirate captains into one of the most successful and tightly knit group of bandits in all of Arrea. 

With Freeport acting as a repair and supply facility for an entire region’s elicit maritime activity, the city’s population boomed. Just as the discovery of minerals or gems can drive the growth of a city, so too can sea piracy. Any sail maker, shipwright, cartographer, or laborer seeking to flee family, financial obligation or legal authority found a home in Freeport. The influx of people soon created a demand for less ship-centered trades, and carpenters, cooks and smiths filled the need. In little over a decade, the town of Freeport had grown into a full-fledged city. 

Though still uncivilized by nearly any measure, Freeport’s unique population created a very peculiar environment. Overwhelmingly comprised of pirates, the people of Freeport were a rowdy lot, but one that put a lot of stock in personal honor. Every citizen knew his job and took a certain amount of pride in calling himself a resident of the world’s most successful pirate city. Sloth wasn’t tolerated, but hard work yielded a pleasant income. Flush with money, Freeport attracted every sort of person – but it also attracted authorities from the mainland. Any nation on Arrea’s eastern coast had a financial interest in the trade vessels that sailed north and south along the continent’s coast. The success of the pirates in and around Freeport soon led to government-sponsored pirate hunting expeditions. These expeditions may have very well spelled the end of Freeport’s reign as Arrea’s pirate capital, if not for a strange and fortuitous turn of events. 

A Chance Encounter

In 295 M.E., an explorer by the name of Captain Lawrence A. Highgrove found himself battling a raging storm. While on a mapping and exploration mission, the veteran captain and employee of the city of Ash-Melin tempted fate and became ensnared in one of the many violent squalls that often arise in the waters off the coast of Lifeswallower. He and his vessel survived the storm, but his ship Champion was severely damaged. His hold full of valuable herbs and spices that he had procured from a group of woodland elves far to the east, Captain Highgrove’s ship was an easy target for any of the numerous pirate vessels prowling the waters in his vicinity. Fortunately for both the good captain and the continued growth of Freeport, the first ship to encounter Champion the morning after the storm was Moonglade, captained by none other than Frederick Hearns. Sensing an opportunity to make a lasting impression, Hearns pulled along side Champion, his pirate colors waving proudly in the morning’s gentle breeze. Highgrove’s crew readied for an assault, but quickly realized that the pirate vessel coming along their port side was not ready to engage them. On the contrary, only 8 hands could be seen on deck, one of them being Captain Hearns. Hearns’ second in command, a half-elf by the name of Harlin Greentree, threw up his signal flags and asked the floundering vessel’s captain if they were in need of assistance. After a moment of thought, Highgrove had his signalman tell the pirates what they already knew – that Champion was without sail and at the mercy of the sea.  A handful of crewmen from Moonglade then threw a line to Highgrove’s crew, and the sailors on each vessel took to securing the two vessels to one another. After Champion was securely lashed to Moonglade’s starboard side, captain Hearns requested permission to board Highgrove’s vessel. Highgrove, with curiosity piqued and nothing to lose, granted permission and Hearns stepped proudly onto Champion’s deck. The two captains exchanged formal introductions and then Captain Hearns announced that, with Captain Highgrove’s permission, he would tow Champion to the nearest harbor and assist in getting the vessel seaworthy.

Three days after this fateful meeting, Champion was towed directly to one of Captain Hearns’ private docks in Freeport Harbor. Hearns provided all of the repair work to Highgrove’s ship free of charge, and Highgrove (and his crew) enjoyed their stay in Freeport as guests of the city’s renowned governor. When Highgrove eventually returned home to Ash-Melin, his stories of Freeport’s people and its leader quickly spread up and down Arrea’s coast. While any pirate who sailed off of Arrea’s eastern coast did so at his own risk, Freeport would forever after enjoy absolute immunity from any military incursion or act of retribution by the mainland governments of Arrea. Freeport’s was officially established as an independent city in the year 296 M.E. when it sent representatives to each of the major cities on Arrea’s eastern coast. As an independent city, and wishing to remain such, Freeport forever after opened its harbors to any and all sailing vessels. Since that time, a safe area roughly 3 days in every direction of Freeport has existed. Any ship traveling through this area is safe from pirate raid. Punitive actions are meted out by pirates upon any of their fellows caught assaulting a vessel within the safe area. 

Captain Hearns’ reign as leader of Freeport ended upon his death on the 19^th of Kadinastis, 321M.E. By that time, Hearns and his government had drafted a quasi-constitution that outlined a method by which all of the captains who owned docks in the city would go about electing a governor. This method for electing leaders has remained largely unchanged through today. Freeport’s growth as a kind of nautical frontier town has continued, allowing countless sailors (some legitimate and some not) to fulfill their dreams of building wealth on the high seas.