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The Free City of Greyhawk, also known as Greyhawk City and the "Gem of the Flanaess," is a fictional city state in the World of Greyhawk campaign setting for the Dungeons & Dragons fantasy roleplaying game. Since the setting was originally published in a folio and then again in a boxed set that were both titled World of Greyhawk, the word "Greyhawk" is often used to describe the entire campaign world setting, although the proper name for that part of the world is the Flanaess. Sometimes the lands controlled by the Free City are also referred to as Greyhawk, though the proper term for the region is the Domain of Greyhawk.

In 1972, after seeing a demonstration of Dave Arneson's Castle Blackmoor game, game designer Gary Gygax agreed with Arneson to co develop a set of rules for a game that would eventually become known as Dungeons & Dragons. Gygax liked the idea of a castle and dungeon that players could explore, and created his own imaginary place called Castle Greyhawk, which he used to test and develop the game. About a month after his first session, Gygax created the nearby city of Greyhawk, where the players' characters could sell their treasure and find a place to rest. The lands around Greyhawk gradually grew into an entire world as Gygax's players explored further and further afield. In 1980, Gygax published details of his home campaign in a folio called The World of Greyhawk. This was the first published information about the City of Greyhawk. The Free City of Greyhawk, Gem of the Flanaess, is the adventuring town that gives the World of Greyhawk setting its name. Game designer Ken Rolston comments: "The City of Greyhawk is an organism of systems within systems, with each system driven by its own motivations and personalities. [ ] External politics are intertwined in the city’s internal affairs. Rival guilds compete for power and influence, and dark conspiracies fester beneath the streets, while less weighty adventures may arise from the lighter aspects of civilized personal and commercial rivalries."

In 1983, TSR, Inc. replaced the folio edition with the World of Greyhawk boxed set, which contained more detailed information about the city and some of its prominent citizens, as well as background information for several small adventures set in the city. By 1983, Gygax was planning a City of Greyhawk publication to be followed by a Castle Greyhawk publication, both to come after the World of Greyhawk Fantasy Game Setting (1983), although the Greyhawk revival began to fade after 1984. The set moved the timeline of the overall World of Greyhawk setting ten years forward to just after the Greyhawk Wars, included information regarding the City's situation, as well as additional adventure cards set in the City. After TSR was taken over by Wizards of the Coast, the World of Greyhawk setting was updated again, and publications of this time period such as Greyhawk: The Adventure Begins (1998), the Living Greyhawk Gazetteer (2000), and Expedition to the Ruins of Greyhawk (2007) also provide information regarding the city in the post wars period.

New Infinities Productions revealed in 1988 that its "Fantasy Master" line had plans to detail both the Castle and City of Greyhawk (renamed as "Castle Dunfalcon") presented in the original form that Gary Gygax and Rob Kuntz had envisioned them, but the company dissolved before any of this went into publication; Applelcline noted that "Gygax's plans to publish the City and Dungeon of Greyhawk in a renamed setting were somewhat fulfilled at Troll Lord Games, who published a few Castle Zagyg books — detailing the uppermost levels of the dungeon — before Gygax's death."

Greyhawk, named for the small grey hawks which populate the region, was originally a trading outpost on the Selintan River specializing in local wood and woven garments. In time the town developed strong textile and meat packing industries. Eventually, Greyhawk came to be ruled by a warlord, who took the title "Lansgraf of the Selintan". His son was then married to the Gynarch of Hardby's daughter. The nuptials formalized a political alliance that served as the basis for rule over the Lanstadt of Selintan, an area that eventually became known as the Domain of Greyhawk. In 4 CY, Greyhawk came under the domination of the Great Kingdom of Aerdy and remained so while strong Overkings ruled from the Malachite Throne in Rauxes. By the 3rd century CY, the Great Kingdom's influence over the city began to wane as the Overkings fell into evil ways and their hold on distant provinces became increasingly tenuous.

Circa 310 CY, the mage Zagig Yragerne emerged from the Wild Coast and bribed his way into a seat on the Directing Oligarchy. Soon after, the Oligarchs elected Zagig Lord Mayor. Greyhawk subsequently rose in fame and prominence under the leadership of Lord Mayor Zagig. He instituted legal reform, developed a new currency, fortified the walls, founded the city's first university and embarked on a major building program. Most notably, he directed the construction of nearby Castle Greyhawk. Although Zagig—later known as Zagyg—became increasingly erratic over time, his rule is generally considered to be the most effective in the Free City's history and brought widespread prosperity to the region. Much to the annoyance of Dyvers and other rival cities, Zagig proclaimed Greyhawk to be the "Gem of the Flanaess," and did much to ensure this moniker was justified. Unfortunately, the "Mad Archmage" suddenly disappeared in 421 CY, leaving no clues regarding his whereabouts, and no heir to inherit the title of Lansgraf. In 498 CY, after decades of Zagig's absence, the Lanstadt was therefore abolished, the title of Lansgraf permanently retired, and the Free City's Directing Oligarchy assumed political authority. The new Lord Mayor Paerinn officially proclaimed Greyhawk a free city, though it had been effectively independent of the Great Kingdom's rule for over a century. Soon thereafter, the city lost its claim over Hardby and the Wild Coast, as the leading women of Hardby broke from Greyhawk and established the ruling office of Despotrix. This loss of lands sent the Free City into economic decline, a situation that persisted for several decades. Fortunately, the discovery of treasure in the dungeons beneath Castle Greyhawk and other nearby locales set off a gold rush of sorts, and Greyhawk's economic fortunes recovered substantially in the second half of the 6th century.

The Free City of Greyhawk actually had less direct involvement in the so called Greyhawk Wars than many political entities across the Flanaess, but because the final truce was brokered in Greyhawk in CY 584, the war has come to be named for the city. The current timeline of the Greyhawk campaign has been fixed as 591 CY, six years after the end of the Greyhawk Wars. The Wars had several important effects on the city, particularly that the unrest drove Hardby and the Wild Coast cities of Safeton and Narwell to re submit to the rule of the Directing Oligarchs. However, since it was largely fear of Turrosh Mak's humanoid raiders from the Pomarj that prompted this move, a situation that has been resolved to some extent, the Despotrix and the Wild Coast cities are once again agitating for increased independence. Also as a result of the Wars, the city has seen an influx of new citizens. Some of these are wealthy diplomats, and some are "nobles" who have contributed significantly to Greyhawk's coffers with the purchase of various counterfeit titles and documents. But many newcomers to Greyhawk are destitute refugees, or are merely using the city as a base for hatching political plots and intrigues across the Flanaess. In particular, there are persistent rumors of covert Scarlet Brotherhood operations in the city. The post war outlook for the Free City is therefore mixed. Greyhawk's finances are in the best shape they have been since Zagig's departure, but the city faces significant challenges arising from political instability and increasing criminal activity.

The Free City of Greyhawk is located centrally in the Flanaess, which is the easternmost part of the continent of Oerik on the world of Oerth. The city controls a large swath of land along the Selintan River from the Nyr Dyv south to Woolly Bay most of the Cairn Hills, parts of the Gnarley Forest, the northern Wild Coast, and parts of the Abbor Alz. The entire region is officially known as the Domain of Greyhawk. The Domain is bordered on the east by the Abbor Alz and its western border lies within the Gnarley Forest. The area south of Greyhawk City along the Selintan is known as the Plain of Greyhawk.

As of 589 CY, the city itself boasted a population of 69,500, making it one of the largest cities on Oerth. The population for the entire Greyhawk Domain is roughly 160,000, including the larger towns of Safeton (pop. 6,100), Hardby (pop. 5,100) and Elmshire (pop. 4,000).

The Free City of Greyhawk hosts temples and shrines to many deities, including Beory, Boccob, Celestian, Corellon Larethian, Ehlonna, Fharlanghn, Garl Glittergold, Heironeous, Istus, Kord, Kurell, Lirr, Moradin, Norebo, Obad Hai, Olidammara, Osprem, Pelor, Pholtus, Procan, Ralishaz, Rao, Saint Cuthbert, Trithereon, Ulaa, Wee Jas, Xerbo, Yondalla, and Zilchus. The worship of evil deities and fiends is forbidden, and such cults, though they may have followers, do not have a public presence. Evil religions that have established a base in the city in recent memory include those of Incabulos, Iuz, Nerull, and Vecna. Many more deities are worshipped in other settlements of the Domain of Greyhawk. See also: List of Greyhawk deities

The most widely spoken language in Greyhawk City and most of the Domain is Common, though other tongues are spoken in settlements with large non human populations, such as Elmshire, Greysmere, and Grossetgrottel.

Greyhawk's Directing Oligarchy elects one of its own to as Lord Mayor, who serves as the head of state in addition to his directorial duties. The current Lord Mayor, Nerof Gasgal, has held office since 571 CY. The Lord Mayor heads both the Directing Oligarchy and the Council of Mayors and Manorial Lords. The chief of state also officially heads the military, though actual command is most often left to the Captain General of the Watch.

The Free City of Greyhawk is ruled by the Directing Oligarchy, an executive council of twelve to eighteen members representing the City's major professional guilds and the military. In some cases, the Oligarchy may include important wizards or clerics. New Directors are chosen by current council members when a vacancy must be filled. The Greyhawk Council of Mayors and Manorial Lords is an annual assembleage of leaders from the various baronies and towns in Greyhawk Domain. In theory, this gathering allows citizens of the Domain to have a voice in the governance of the region, but in practice this Council has little real authority.

Major legal matters in the Free City of Greyhawk are adjudicated by a Judge of Greyhawk, one of eight such officials appointed by the Directing Oligarchy. One of these eight is chosen to serve as Chief judge of Greyhawk, a position currently held by Sir Anton Palmirian who also sits on the Directing Oligarchy and oversees the Guild of Lawyers and Scribes. In cases of great import, three Judges of Greyhawk may preside. Appeals of major cases are always heard by a panel of three Judges of Greyhawk, though the Lord Mayor sometimes sits in place of one of the Judges. Lesser matters in Greyhawk City are tried by magistrates from the Guild of Lawyers and Scribes.

The city's coat of arms is blazoned thus: Sable, a castle triple towered argent, in chief two chains each of four links chevronwise of the second, in base six bezants.

The Free City of Greyhawk controls most of the Cairn Hills, which provide the domain with great mineral wealth, such as iron, gems, and silver. Nearby Castle Greyhawk, with its extensive dungeons, draws adventurers and traders to the Domain of Greyhawk from across the Flanaess. As such, the Castle generates significant economic benefits for the City in trade, taxation and treasure.

The Domain of Greyhawk's standard coinage consists of the platinum plate (pp), gold orb (gp), electrum lucky (ep), silver noble (sp), and copper common (cp). All of the coins are round, except for the platinum plate, which is square. The current coinage system replaced the previous system, which included coinage worth less than the copper common known as bronze zees, brass bits, and iron drabs.

Several roads link the settlements of the Domain of Greyhawk, including the High Road (from Greyhawk City to Elmshire), the Urnst Trail (from the High Road to the Duchy of Urnst), the Western Road (from Ford Keep on the Selintan to Dyvers), and the River Road (south from Greyhawk City along the Selintan). Much river traffic takes place along the Selintan River, which can accommodate all but the largest sea going vessels from the Nyr Dyv and Woolly Bay. Smaller vessels ply the Ery and Neen rivers.

The Able Carter is a coach company created by author Erik Mona, which first appeared in the 2000 RPGA adventure module, River of Blood. It has coaching inns in Greyhawk City, Hardby, Diamond Lake, Blackstone, Elmshire, Steaming Springs, Narwell, Safeton, and Dyvers, among other locations.