Gloomnight is the largest city in the Shadowlands and the oldest as well. Unlike other Elthedar cities, it was transported into Shadowlands only partially destroyed, so it was inhabited from the birth of this realm. Therefore, Gloomnight is a crumbling, sprawling, decadent, corrupt city, with history that stretches thousands of years - a city that outlived several nascent empires which ruled it, and continues to exist in some kind of urban unlife. This is a dark place. Some of the city's most interesting locations are: Hag Market, where you can haggle with Hags and deal with the Devils; Old Court, where vampires dance to the silent music and trade in blood and dreams; Slaveport, located at the confluence of two great rivers, where barges bearing fresh slave-meat from East and West unload their cargo; Nightingale Street, where you can find any and all pleasures known to man or dragon; Old Dungeon, located beneath ruins of Constabulary, filled with corpses when the Great Plague struck the city; Troll Bridge, built by Trolls at the bequest of Lord Mayor and in return they got the toll rights and land to build their slums across the Great River; Despot's Hold, overlooking the rivers, but without any lord living in it.
Gloomnight is essentially divided in two parts - Gloom and Night. Gloom is the part of the city which is above ground, and Night is underground part of the city. These two parts are interconnected in many places, some of them controlled by the Great Houses, some of them free to use by anyone. Gloom is a dismal place of twisting lanes, narrow alleys and chaotically placed houses and haphazardly built towers. In the center of Gloom there is an impossibly tall castle, with many pointed spires, easily the size of Teros Obsidia. This is Despot's Hold - the seat of ultimate power in the city, now without owner for a very long time. Person who controls the Hold controls the Gloomnight; person who controls Gloomnight controls much of Shadowlands, so the Hold is contested amongst the Great Houses. Currently, the Hold is under joint stewardship of House Garganth and House Borzar, but they do not rule it. It is said that the ruler of the Hold must be accepted by the Throne of the Hold, an ancient artifact - possibly a remnant of the world before the Fall.
Power in the city is divided amongst Houses, both Great and Lesser. Houses of Gloomnight are something between noble families, guilds and criminal gangs. Each Great House is dominated by one race, but all the Houses have members of various races, who are fighting for influence inside their House. Current Great Houses, with their dominant races, colors and the description usually applied to them are:
Golgoth - NE Black/Green Shadar Fleshwarpers
Morai - NE Black/Blue Morgral Assassins
Zim - N Blue/Red/Green Goblinoid Alchemists
Garganth - NG White/Blue Gargoyle Sentinels
Zelenya - CG Green/White Beastpact Earthkeepers
Rajarr - LE Black/Red Tiefling Slavers
Borzar - LN Red/White/Blue Asimar Mercenaries
The daily life in the city is centered around markets. There are several of those: Hag Market, where you go if you want to buy a broken dream, discarded wish, magic sword or slightly-used soul; Goblin Market, where you can buy everything from food to weapons made by goblin smiths from the Coldmist Mountains; Slave Market, near the River Port; Hold Market, which is now defunct - as well as several other smaller specialized markets. Several fay have their stalls at the market or shops around the market square, as well as alu-fiend twins, Mayala and Nayala, who mostly deal in poisons and potions.
There is a large Hag comunity in the city. A prominent member and sort of unofficial leader of Hag Market, is a Hag called Baba Svetlana. She's 900 years old and rather uninterested in good or evil. She trades equally with all and nobility often buys from her. She sells, among other things, used wishes, one night stand frog princes, slightly rotten pumpkin coaches and awakened mice bodyguards. Svetlana is little above it all. She's old enough not to have to work and equally old to acquire a cynical view on both good and evil, so she drifted towards neutrality. If she's the owner of your character's contract, she would use him mostly as a messenger or a spy. These days Svetlana mostly trades in information, but she's always interested in some new magic item (or old and powerful), piece of property in the city and her not so secret passion is collecting (and reading) love novels and ballads from the Twilight's court.