The third largest city in all Varisia, Riddleport is also the most notorious. Once a secret pirate haven, Riddleport has grown over the last three centuries into a port city in its own right. At first it served as a den of piracy, but over time the city has expanded into a true settlement, the frontier’s frontier, the northernmost outpost on the lonely strip known as the Lost Coast. Yet while Riddleport has grown into a proper city, it remains true to its roots—you can get rich quick in Riddleport if you’ve got skill and a bit of luck. Yet, for every Riddleport success story, there are a dozen nameless bodies buried in potters’ fields or tossed to the hungry denizens of the sea.



Large City nonstandard (titular overlord with multiple crimelords);
GP Limit 40,000 gp; Assets 26,600,000 gp
Population 13,300
Type mixed (77% human, 7% dwarf, 5% half-elf, 4% half-orc, 3% tiefling, 2% halfling, 1% gnome, 1% other)
Authority Figure
Gaston Cromarcky, NE male human fighter 7/expert 5 (Overlord of Riddleport)

In-Depth Map of Riddleport

Riddleport at a Glance

Most of Riddleport’s buildings are composed of wood— logs or planks—with multiple floors and steep, highpeaked roofs of wooden shingles. They are built in close quarters, and in some cases their wooden upper floors sag and lean together from the constantly sodden conditions. Stone fireplaces ward off the bitter winter cold and the chill that lingers in the fog-laden streets for much of the year, save for in high summer. During this two-month period, warmer air currents from the south bring a muggy, oppressive heat along with great black mosquitoes that breed in the nearby marshes. Many burn peat treated with incense in their hearths during these months to ward off the vermin with their thick smoke.
The major streets of Riddleport are cobbled, often becoming rain-slick cataracts during the wet seasons. Cobbles are often missing or crushed by the incessant traffic, leaving gaping holes and ruts in even the most well-tended thoroughfares. Side streets tend to be relegated to muddy tracks that are swift to turn into stinking morasses of sucking mud and filth. Riddleport doesn’t have much of a sewage system, and relies mainly on gutters along street edges to carry refuse to the river and harbor. One feature unique to the major streets are the frequent oil lamps mounted on iron poles that provide beacons of light in the benighted mists. These are set in sturdy hurricane lamps and burn thick, rancid-smelling oil from barrel-shaped reservoirs at the lamppost base—a byproduct and innovation of the Gas Works. These wavering lights give off illumination equal to a torch in even the foulest weather but are not well-tended; just over a third of them are out on any given night, in need of repairs or refueling.

Life in Riddleport

The titular head of the Riddleport government is the selfappointed Overlord of Riddleport, a position traditionally held for life. Riddleport’s current overlord is a former pirate captain named Gaston Cromarcky. Since the city’s founding, Riddleport has been ruled by a series of pirate lords, buccaneers, and other unsavory sailors in a bloody cycle of betrayal and violent coups. Overlord Cromarcky has maintained his rule over Riddleport for three decades by entrenching himself in a wholly new manner. Rather than rely on the loyalty of pirate crews and fellow captains, Overlord Cromarcky opened the coffers of his deceased predecessor and hired mercenaries and enforcers from land-bound groups with no connection to piracy. Calling this new breed of enforcers the Riddleport Gendarmes (“gentlemen-at-arms”), he created a military force loyal to his coin.
Under Cromarcky’s rule, life in Riddleport has become more stable than ever before. Open streetwarfare between rival gangs is a rarity now, and the gendarmes have made it safe enough for brave or desperate merchants from Magnimar to bring in trade. By Overlord Cromarcky’s decree, any ship that flies the flag of Riddleport at full mast is under his protection and is not to be raided by any pirate who wishes to call Riddleport home. That Cromarcky charges scandalously high prices for this protection of visiting ships ensures that there’s always enough ships plying the Lost Coast or the southern waters for Riddleport’s traditional pirates to prey upon to keep them happy. The stability and semiregular influx of imported goods has begun to spoil the citizens of Riddleport, but these days may be numbered. Rumors abound that Cromarcky’s coffers may finally be running low (despite his protection racket), and the rise in power of Cromarcky’s most vocal public enemy, Elias Tammerhawk, has many of Riddleport’s citizens expecting a shift in leadership soon, an eventuality that many Riddleport traditionalists would greet with relief. Despite the unheard-of political stability that the city of Riddleport currently enjoys, only a longtime Riddleport native would ever think of the city as truly civilized. The overlord rules with a light touch and with the consent of several powerful individuals who likewise shape the direction of Riddleport’s future. These individuals are the various crime bosses who hold sway in the city. Pirates may have founded the city, but many more bandits and scoundrels soon saw the value of having a place to call home, the wilds of Varisia hardly being a safe place to camp. The crimelords each have their own particular specialties and focus, and they play the role that noble families do in most other cities: they are the movers and shakers, the leaders whom the average citizen idolizes and fears. When an overlord dies, the new overlord invariably rises from the ranks of the city’s crimelords.
Yet not everyone who comes to live in Riddleport is attracted there by the promise of loose law and criminal sanctuary. In increasing numbers, all manner of sages, scholars, and wizardly types have been flocking to the city, drawn by the presence of the Order of Cyphers. This scholastic organization is dedicated to deciphering the mysteries of ancient Thassilon’s monuments—in particular, the vexing Cyphergate, whose function and meaning have eluded illumination for so long. The locals find the influx of philosophers and scholars aggravating, and find their soft-spoken ways and general attitude to be infuriating, but the Order of Cyphers does not interfere with the day-to-day skullduggery of Riddleport’s citizens. Furthermore, Overlord Cromarcky has openly welcomed the order to Riddleport, likely because the addition of many skilled wizards can only increase the city’s defensive options. That the leader of the Order of Cyphers went on to be Cromarcky’s most outspoken public foil no doubt vexes the aging pirate lord, and many of the city’s citizens have taken to betting among themselves on how may more weeks will pass before Cromarcky and Tammerhawk come to blows.

City Districts

Riddleport is divided into a total of nine separate districts (although two of them, Lubbertown and the Boneyard, technically lie outside of the overlord’s jurisdiction):
Free-Coin District: Overlord Cromarcky’s three grand gamehalls are located in this part of the city along the northwestern shore of the Velahsu River.
Leeward District: The city’s largest district, Leeward is built into the protecting curve of the city’s eastern ridge, where it is sheltered from the worst of the winter winds. The majority of the city’s population resides in the tall tenements of this district, and most buildings have a shop at street level where standard goods and services can be obtained.
Lubbertown: Known derisively as Lubbertown for the fact that most of its inhabitants arrive at the city by land rather than by sea, this district is not patrolled by the gendarmes and has developed its own social order, informal system of laws, and distribution of goods and employment.
River District: This section of town runs along the banks of the Velashu River and consists primarily of shops and mills. Riddleport’s atrophied trade items are crafted in this district. The waste produced by the district’s tanners and fishmongers and the fact that many of the city’s sewage gutters converge here have earned the place the unofficial name of “Reek District.”
Rotgut District: The slums of Riddleport are a truly depressing and dangerous place to be. Easily the poorest section in the city proper, Rotgut also hosts the highest crime rate and the most brothels and alehouses per capita. It lies along the city’s eastern side against the ridge.
The Boneyard: This deceptively named place actually serves as the city’s dump and ship’s graveyard. Its name is derived from the many old hulks and collections of ships’ ribs that protrude from the swampy ground. The whole area is a partially flooded salt marsh that is generally 2 or 3 feet deep, although some hidden patches of quicksand are much deeper. Monstrous cockroaches, swamp barracuda, and (it is whispered) wererats infest this area.
The Devil’s Fork: This small military district is nestled near the north end of the city on an island in the Velashu River. It serves above as barracks for Riddleport’s 250 gendarmes, and below as a prison for the city’s malcontents.
Wharf District: This rough-and-tumble district lies hard on the edge of the very docks of the city and is where much of the city’s day-to-day action of commerce and thievery occurs. Nearest the docks are a series of warehouses and cheap grog houses where merchant and pirate crews alike mingle in a haze of rum-soaked blood and debauchery.
Windward District: Built on the slopes of the city’s western ridgeline, this is Riddleport’s affluent district; the buildings here are generally quite tall and its streets winding and steep. The majority of the city’s scholars and sages dwell in this windy district.

Important Sites

Several of the more important locations in Riddleport are described below.
In-Depth Map of Riddleport

City Mortuary: This large, nondenominational chapel is maintained by the churches of Cayden Cailean, Calistria, and Besmara, and is used for funeral services and burial rites. It features its own attached mausoleums for those who can afford interment there rather than in the common graves of the Burying Ground.
Cypher Lodge: This lodge is the headquarters of the vaunted Order of Cyphers, a society of skilled wizards and sages who have dedicated themselves to unraveling the secrets of ancient Thassilon—in particular, the purpose of the Cyphergate. The lodge is open to all cyphermages for a monthly room-and-board fee of 1 gp, a fee that grants access to its extensive libraries as well as a host of learned scholars on the subject. To non-cyphermages, a day’s room and board (and access to the libraries) is a much heftier 20 gp. Nevertheless, its guest rooms are almost always full.
Cyphergate: The enigmatic Cyphergate looms large over Riddleport’s harbor, a constant reminder of the transience of life and even civilization, since no record has ever been found of who may have raised this architectural wonder. The arch rises 350 feet above the water at high tide, secured by the rocky crags on either side of the harbor mouth—its diameter is exactly 700 feet. It is of an unidentifiable stone of nearly supernatural hardness that resists almost all efforts at defacing or marking, and as with most Thassilonian monuments, it has weathered the passage of years amazingly well. Most scholars believe that the runes on the arch have no meaning, and are decorative. Magical attempts to decipher the runes have supported this theory, yet the Order of Cyphers believes that this simply points to the runes’ mystic nature, that even magic cannot decipher their meaning or the Cyphergate’s true purpose. Cracking this code has become the primary goal of the Order, yet they are no closer to solving it today than they were when their order was founded.
Gas Forges: This immense building, said to be built over a large deposit of rare natural gas, is owned and staffed by dwarves. The forges within are the only ones in all Varisia that burn hot enough to smelt and forge certain rare metals like adamantine.
Gold Goblin Gambling Hall: Once a high profile venue and shining diamond of the bustling Wharf District, this run-down gambling hall has been recently rebuilt and is the site for the upcoming “Cheat the Devil and Take His Gold” gambling tournament.
House of the Silken Veil: This octagonal pyramid is the city’s temple of Calistria in addition to being a highclass brothel. Temple prostitutes work the streets and squares of Leeward and send criers and samples down to Wharf District to bring in the “pigeons.”
Maskyr’s Island: Named for Cabriem Maskyr, the pirate captain who became the first overlord of Riddleport, this islet in the center of the Velashu River holds the current overlord’s citadel and estate as well as many of the city’s various administration buildings. Several docks provide access to the island, but all are heavily guarded by gendarmes. Overlord Cromarcky does not accept visitors lightly.
Publican House: A sign bearing the symbol of a dented ale mug hangs above the door, and written discreetly beneath it in gold letters are the words “Publican House.” This raucous place is actually a temple to Cayden Cailean, god of adventurers and drink, and is a favorite among the ships’ crews and travelers that visit Riddleport for its fair prices and wide selection. Cyphermages are not welcome here.

People of Riddleport

Over ten thousand souls call Riddleport their home, but very few of them actually have any real positions of power. Some of the city’s more notorious folk are detailed below.
Anton Mescher: Overlord Cromarcky’s right-hand man, Anton oversees the city’s fortress-prison and leads the gendarmes.
Arnando Rolf: Arnando is the high priest of the local temple of Cayden Cailean, a bear of a man who is rarely seen without a notched sword swinging at his hip.
Avery Slyeg: The owner of a pricey inn called the River Runner, Avery Slyeg’s true interests lie in smuggling and other black-market operations; it’s said he has agents in two dozen cities throughout the Inner Sea region.
Boss Croat: Known for keeping entirely half-orc minions, Boss Croat has his hand in much of Riddleport’s drug trade and other contraband.
Clegg Zincher: One of Riddleport’s more notorious crimelords, Clegg runs the quite profitable Zincher’s Arena, a place where anyone can pay to see desperate men fight monsters (or, more commonly, each other).
Elias Tammerhawk: Elias is the leader of the Order of Cyphers, an accomplished wizard who has been elected as speaker of the order for two consecutive eight-year terms. Many whisper that Elias has his eye set on the position of overlord, and Riddleport’s other crimelords worry about the nature of the changes to their beloved city should this event occur.
Gebediah Krix: Gebediah, rumor holds, consorts with fiends from the Outer Rifts. He runs the Riddleport Light, and does so responsibly enough that the overlord has left well enough alone. Visitors are not welcome here.
Grimas Oltedler: Grimas runs the Velashu Ferry, the only safe mode of public transport over the river. He works steadily through the evening and night but must be summoned from his bed by ringing the ferry bell if one is seeking passage before midday. Prices range from 2 to 6 copper per traveller, depending on the length of the journey up or downriver.
Hyram Crooge: Hyram is a reclusive man who dwells just outside of town on a ledge overlooking the Boneyard. He maintains a constant bonfire for the burning of some trash and dumps the rest over the cliff edge into the marsh below.
Lymas Smeed: This surly man is one of Riddleport’s more notorious moneylenders. Lymas Smeed (if the streetside chatter is to be believed) feeds parts of those who fail to pay him back on time to his alwaysravenous pet baboon.
Ruben Carfay: A retired sea captain, Ruben is the leader of an open-air temple dedicated to the Pirate Queen Besmara.
Saul Vancaskerkin: Just recently, Saul recovered his footing in Riddleport after several years of destitution due to some sort of run-in with the other crimelords of the city. He’s recently purchased and rebuilt the Gold Goblin Gambling Hall.
Shorafa Pamodae: An alluring but dangerous tiefling high priestess of the temple of Calistria, Shorafa is also one of the city’s minor crimelords and rules the hospitality industry, from pimps to liquor sales.

A Primer on Riddleport Slang

Many of Riddleport’s citizens have their own slang and jargon that they use in mixed company to hold conversations in front of others while not revealing what they’re actually talking about. Of course, in a city of thieves, the Thieves’ Cant loses much of its use, and over the years, the Cant has devolved into a wide collection of regional slang words that most folk pepper liberally (and without thinking) into everyday speech. Listed below are several of the more common bits of Riddleport Slang.
Abbess: A priestess or whore of Calistria
Bridge Monkey: Someone from Magnimar
Capp: A trusted lieutenant or henchman
Cattle: A group of Varisians
Cow: A Varisian
Church Work: Any lengthy job that is slow to finish or is otherwise drudgery
Dog Biter: A large rat, small child, or halfling
Earth Bath: An unmarked grave
Easy Lad: A male prostitute
Fancyboy/Fancygirl: A cyphermage (sometimes an elf )
Gendarme: A city guard
Grog-Blossom: A facial pimple, or an unsavory person
Hushman: A hired killer, generally one kept on semipermanent retainer
Kiss: To stab someone—“Kissed the snickersnak” is a phrase used to mean “Got murdered”
Laced Mutton: A prostitute (gender neutral)
Leaky: Someone who can’t keep a secret (“Don’t tell him about the heist—he’s leaky!”)
Lumber: A passenger on a ship (typically an unwanted or unwelcome passenger)
Pigeon: A person targeted by a criminal to be the victim of a crime, or a person that visits a prostitute
Pigmeat: A dead body, or someone who is about to become dead
Pump-Sucker: A dwarf (particularly one who works at the Gas Forges)
Quickwife: A female prostitute
Rathole: The mouth (especially a mouth that belongs to someone who is saying unwelcome things)
Rotgut: Liquor (particularly foul-tasting liquor)
Sideshow: A tiefling
Snickersnak: A small knife that can be easily hidden on a person’s body
Soaker: A priest of Cayden Cailean
Soggy Plum: A drunk
Whisker: A wererat

Deities of Riddleport

Although not a particularly pious lot, the people of Riddleport know better than to trust in luck alone. Thus, a number of unruly congregations flourish in the City of Cyphers, the largest being dedicated to deities sympathetic to sailors, gamblers, criminals, and free spirits of all walks.
Besmara: Although primarily worshiped among the Shackles far to the south, the Pirate Queen is the goddess of pirates, strife, and sea serpents. Thus, her faith suits the scallywags and seafarers of Riddleport well. Her temple, derisively known as the Fish Bowl, makes regular blood sacrifices to assure safe and profitable voyages.
Calistria: The fickle goddess of trickery, lust, and revenge maintains a particularly healthy following in Riddleport. Her temple, the House of the Silken Veil, encourages her flock’s vendettas and oversees the city’s “hospitality” industry. Several thugs and assassins are known for quoting Calistria’s collection of holy poems, Blood for Wine, before setting about their grim work.
Cayden Cailean: From the raucous Publican’s House, the clergy of Cayden Cailean, god of alcohol, bravery, and freedom, welcome nearly all comers and hearten those who seek to live lives free of laws and restrictions. The church of the Drunken Hero is known for helping newcomers find homes within the city and encouraging legitimate trade—especially the import of exotic wines and brews.
Desna: The most blessed and cursed deity in Riddleport, the butterfly-winged goddess of travelers, luck, and the stars watches over gamblers, navigators on ships, and those seeking fortune and new beginnings. Although her faith does not support an actual temple within the City of Cyphers, nearly every gambling den in the city bears a statue in her image and several wandering priests—particularly of Varisian descent— do her work.
Gozreh: Although no temple in Riddleport bears the symbol of the Wind and the Waves, few sailors don’t in some way pay respects to the god of nature. Many docks bear small shrines so departing seafarers can offer last-minute sacrifices, and wandering clerics and druids of Gozreh sell blessings and prayers for their god’s distraction.

Riddleport Rumors

In a city where everyone watches for new opportunities to turn a profit, no news remains a secret for long. Here are but a few of the rumors currently making the rounds in Riddleport.
The Shadow in the Sky: A strange, persistent, dark cloud recently appeared in the sky above the City of Cyphers. Some people say it was caused by the Order of Cyphers meddling with the Cyphergate, while others believe it’s a storm being cooked up by Gozreh or some overly moral deity to wipe Riddleport off the map. It’s the big news in town and everybody seems to have their own explanation.
Carnivore Carnage: Several Shadde-Quah wavecutters recently washed up on the rocks near the Riddleport Light, their hulls covered in dozens of gashes from teeth and claws. Sailors fear some new predator in the Varisian Gulf or an unseasonable migration of local bunyips.
The Devil and His Gold: The washed-up crime boss Saul Vancaskerkin recently renovated the Gold Goblin Gambling Hall and has a massive gaming tournament planned called “Cheat the Devil and Take His Gold.” While this might just be a publicity stunt, some say the swindler sold his soul to some fiend and is using the tournament as a way to raise the money to buy it back.
Lost Below: Milon Chath, a cleric of Desna, left to explore several caverns in the nearby Calphiak Mountains more than a week ago and has yet to return. Several Varisians fear the priest has become lost in the labyrinthine caves said to riddle the endless depths below the mountains.
Siren Song: A band of smugglers recently tried to set up a base at Devil’s Elbow, an island just south of Riddleport’s harbor, but they’ve gone missing. Most blame Virashi, the famed siren of the haunted island, for the disappearance.

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