The Screaming Gate
Located roughly 1000 miles from the base of the Spire in the Outlands, situated between the gate towns of Torch and Curst, sits Hopeless, the gate town to the Grey Waste. Hopeless is a colourless pit of apathy, a grey tinged spiral of depression that leads down to the gate to the Wastes at the centre of it. The town sits surrounded by land more akin to the Three Glooms than to the Outlands, with the terrain no longer flat, but corrupted with rocky hills and twisting ravines before rising into mountains beyond the town.
Little of the town resides on the surface of the plane besides the brilliant, blood red stone gate that marks the only entrance and exit of the town. The screaming gate, as it is called, opens to a single broad street that spirals down into the earth, eventually reaching a courtyard with the gate to the Grey Waste. If nothing else it makes things in the town immeasurably easier to find, and also nearly impossible to hide from pursuit.
All the buildings in the burg flank the single descending street, composed of weathered gray wood, and pitted grayish stone. No colours mark the town save for the screaming gate and the dreary, melancholic air that hangs over the town only worsens as one descends down the spiral road, deeper into the city. Everywhere the situation is the same: depression, gloom, and apathy to mirror that of the Grey Waste itself.The pall that hangs over the town strikes at both the architecture and the people who call the burg kip. Depression and apathy is worn by the residents like a tattered, smothering cloak, and while the city reeks of evil at times, most residents simply don't have the energy or motivation to be cruel to any visitors.
The longer one stays within Hopeless, the harder the proximity to the Waste affects the poor sod. The skin takes on a gray, unhealthy pallor, known as a Wasting tan, and the eyes become sensitive to the presence of any colours beyond gray and soft black. Because of this, the ruler of Hopeless has decreed a literal dress code, restricting permissible colours to a thin spectrum of shades of gray. Deviation from this is the most common way for a newcomer to Hopeless to fall afoul of the citizenry, and then the town watch, including the beholders. The citizens may first only scowl and curse an offender, but progressing further into the town, or lingering with the bright colours may eventually provoke a mob of angry bloods throwing mud,stones, and even worse at the clueless.
Little in the way of past time exists in the town beyond the taverns that cater drink to travellers and those depressive citizens who've taken to bub to inure themselves to the persistent gloom. The only other notable event to occur semi commonly in the burg to draw the attention of the citizens in any large numbers, are the frequent executions performed by Thingol the Mocking on those who've fallen afoul of her laws or simply offended her in some manner. These take the form of anything from being suspended telekinetically by two beholders, whilst a third disintegrates them one layer of flesh at a time, to being slowly turned to stone, the affected areas slowly shattered, and being returned to flesh for brief periods in between. Before these brutal executions, the offenders are always allowed a chance to perform on the large public stage situated next to Thingol's palace at the first entrance nearest to the Screaming Gate, formerly the site of a large orphanage. So tales go, if the offended can in any way during their performance before execution, make Thingol feel any emotion at all, she will commute their sentence. The string of executions is long.
Hopeless is nominally ruled by a masked female human who goes by the name of Thingol the Mocking. Her rule is enforced swiftly and harshly if need be, by a large number of armed and well-trained thugs, and most impressively by the seven beholders who constantly float over and patrol the spiral street of the burg. The town adheres to the rigid guidelines set out by Thingol for fear of her beholders and the slow, excessively cruel and very public executions she relishes in holding for any who disturb the status quo.
Thingol the Mocking, the High Cardinal of Hopeless, is never seen without her bestial, snarling, wolf faced iron mask and her ever moving, dancing cloak of chains upon her shoulders. None have ever seen her face, hidden by iron mask and ebony hair, so it is said, not even her Beholders. But whatever visage lurks behind the mask is cruel and pitiless as the Three Glooms that lie so close through the gate that sits a scant 30 yards from her palace. When she speaks, her voice seems to project forth from the mask with a booming, commanding resonance, and woe to those who reject her dictates.
The seven beholders under Thingol's command are bound to her in some way, either through enchantment, owed debt, shelter from the beholder's enemies, or some other reason which remains dark. The eldest of the seven, Xarcoriax, nearly double the size of the others, is never seen more than a block away from Thingol's palace and is rumoured to possess some measure of control over his brethren or telepathic link to them at all times.
Thingol's soldiers range from battle hardened former mercenaries in the blood war, to run of the mill street toughs with no formal training in fighting. Of the former group, their leader is a blood by the name of Jerican Blackblood, supposedly a former member of the cross-trading mercenary army of the lower planes "The Infernal Front". He answers such questions about his past with a steady hand on his sword and a glare to chill a Gelugon. He serves almost as an intermediary between Thingol and the less trained of her guard, and it is clear that he detests the lack of discipline among many of her soldiers.

Map of Hopeless

 1. The Screaming Gate
 2. The Chapterhouse of the Sisterhood
 3. The Defenestrated Paladin
 4. The Castle of Bone
 5. The Open Tomb
 6. The Palace of Thingol the Mocking
 7. The Gate to the Grey Waste
 8. The Flayed Petitioner

The Gate
The Spiral Courtyard stands at the lowest end of the burg's single, descending road, paved in scuffed gray cobblestones that seem pitted and etched as if by acid. Here, where the gloom seems thickest and most oppressive, in its centre stands the gate to the Grey Waste that will deposit a seeking, or unfortunate blood onto the layer of Oinos. The gate takes the form of a deep, decrepit circular pool plunging into the earth filled with a liquid best described as a cold, liquid tar. With the correct gate key, plunging into the well will send a cutter through the gate, or the liquid can be commanded to flood out of the depths and immerse most of the courtyard to enable the transport of larger numbers of people or items.

Chapterhouse of the Sisterhood
The Chapterhouse of the Sisterhood, contrary to the name, is an umbrella group of good aligned cutters who've come to Hopeless of their own free will to minister to the poor wretches who dwell in the city, unwilling or unable to leave the gloom. They are led primarily by an aasimar cutter by the name of Jerison Kasmat as well as Dianna Ormoland, and Arturus Fennisflame. The chapterhouse stands some three stories high, of smooth gray stone that stands out as soothing, whereas all the other buildings of the same construction seem depressive. The building is surrounded on all sides by high-buttressed walls, and the gate is constantly guarded. While the group abides by Thingol's laws, they are hated by many of the citizenry for their actions, though Thingol makes no official comment. Inside the group provides healing, rest, food, and advice of most any sort by those willing to ask, and they patrol the burg's streets, collecting the bubbers and the hurt and bringing them back for whatever aid they can provide the unfortunate. But they never leave the confines of the Chapterhouse without their own heavily armed escort.

The Defenestrated Paladin
Widely known as the rowdiest inn and tavern in the city, this long, twostory building of soot covered wood and stone sits near the centre of the third ring of the city. It is owned and run by Vrikus Mel'Ort, a dusky skinned tiefling of mixed or otherwise indeterminate fiendish heritage, who manages to keep the fights and spilt blood to a minimum, or at least keep it confined to outside the inn, where the troublemakers are as likely to be disintegrated on the spot by one of the High Cardinal's beholders than settle their fight amongst themselves.
The inn caters primarily to non-residents of the burg, those with some sense of emotions and motivation enough to contribute to the atmosphere within. Fiends abound here, as much as they do anywhere in the city, but it seems a preferred spot for them and mercenaries travelling to the Waste to join with other groups bound for the Blood War in a circuitous route.

The Open Tomb
Well situated in the middle of the 3rd ring of the city sits the low, one story, mausoleum shaped tavern called the Open Tomb. The mix of patrons tends to be half citizens of Hopeless, and half outsiders, but more the outsiders who don't wish to cause trouble, or seek anything more than a meal and a room for the evening. The inn tends to be as silent as the namesake.
The owner is a silent, melancholic woman with a long swath of waist length silvery gray hair who goes only by the name of Ashen Sirah. While some remark that given the name of the tavern, its shape, and the proprietor's disposition, she might have once been a member of the Dustmen, it's more likely her lack of emotion and passion is simply the result of having lived within Hopeless for many years. Or as others rumours have it, that she was a former member of the Bleak Cabal who lapsed into the Grim Retreat and only the emotional sapping of the burg keeps still the more outward show of her insanity. She's not one to hold much of a conversation, so while the ale may flow, her tongue does not and the truth remains dark.

The Castle of Bone
This thin, three story circular tower of stone, carved to resemble a collection of piled and stacked bones, sits near the end of the first ring of the gate-town. Of all the inns of the city, it is rumoured to contain the most rumours, chant and darks for those bloods who'll spend the jink here for bub, a meal, and a room for the night. It caters mostly to travellers in the city, and more unusual kinds as well, from adventuring bands to graybeards and sages to, as the same rumours say, an avatar of the Torilian god Cyric who frequents the inn to torment the patrons.
The rather unique and rarely seen owner of the establishment is a rail thin but seemingly young tiefling by the name of Kestrin Ulket. The times he frequents his own establishment he makes a show of speaking with the night's patrons and mingling with the crowd, likely seeding the floor with the very same rumours that make the establishment profitable. How he comes by those that happen to be true is another question entirely.

The Palace of Thingol the Mocking
The palace of Thingol the Mocking, High Cardinal of Hopeless is a collection of towers, spires and manors that sprawl in a grand complex from the depths of the spiral courtyard out to, and over in colossal stone archways the 5th, 4th, and 3rd rings of the ever descending spiral road. The only public entrance to the Palace sits at the base of the spiral, abutting the Spiral Courtyard and is heavily guarded by Thingol's soldiers and at least one of her seven beholders at all times. Several of the spires that rise above the Palace have open archways built into the stone, presumably for the beholders to enter and exit the domain of their mistress at their leisure. The palace can be seen from anywhere in the city, being a constant reminder of the desolate, and nigh unchangeable situation within the town that citizens come to accept as it is daily reinforced upon them if needed, and even if not.

The Flayed Petitioner
Nestled quietly on the southern end of the spiral road sits the remains of the Flayed Petitioner. The tavern used to cater for a fairly rough bunch of bashers with various fiends passing through the town using it as a place to kick up their heels and throw back some bub. Chant was that a good many deals revolving around the Blood War were made in its grimey interior, and as such it was always closely watched by Thingol's beholders and the town guards. It was rare for trouble to break out in full though - those who used it found it to be a valuable resource and did not wish to risk its loss.
However, it all came crashing down recently when a disagreement between a Cornugon and his Barbazu troops and a petty Marquis Cambion escalated out of control and a huge open brawl broke out. Many of those in the tavern were slain in the cross-fire, especially once two beholders showed up and began disintegrating everything that moved. When the dust settled the tavern was a gutted, broken shell of a building. After the beholders had finished disintegrating the dead all that remained were blood stains and broken furniture. Del Araquid, the tiefling owner of the Flayed Petitioner was killed in the fight; or at least it is assumed he was killed (i.e. disintegrated) as his body was never found, and as a result the building now sits empty with the doors boarded shut.