Have you MC’d a game of Dungeonworld, and had problems coming up with a detail from an overworld map? As per a crossposted suggestion I had in a previous thread, perhaps treating the landmark as an AWish hardhold can help you out.
Because we are playing Dungeonworld, start by asking yourself where this landmark is adjacent to a horrible dungeon.
Does the city in question lie adjacent to a horrible dungeon? If yes, then this city is a dungeonhold. A dungeonhold has:
1) Three to five dozen people.
2) Trade in subsidence farming, trinket bartering, corpse scavenging, and day labor. (+Hunger)
3) A wooden pallisade, and maybe a keep or a motte and bailey.
4) An armory of simple weapons and enough arrows and missiles for a skirmish.
5) A militia of around 1 or 2 dozen irregulars.
6) A dungeon, which is filled with ugly demihumans guarding a basket of trade goods and martial weapons.
Pick three from this list:
1) The dungeonhold is huge, seven to ten dozen people large, and protected by a stone wall.
2) The dungeonhold is tiny but proud. Six noble people are ensconced in a stone keep and fed by their twelve house people. (+Intrigue, -Hunger)
3) The dungeonhold is a thieves haven. The syndicate here fences, smuggles, raids merchants, and blackmails neighboring hamlets. (+Reprisals)
4) The dungeonhold is growing, and features a smithy, craftsmen, a market square, and a plantation. (+Idle)
5) The dungeonhold is intimidatingly secure, with iron gates, an armory of martial weapons and countless missles, and a moat.
6) The dungeonhold has a dungeon with fabulous treasure, lost secrets, or untold magicks. (+Adventurers)
And three from this list:
1) The dungeonhold is wholly foul. (+Curse)
2) The dungeonhold is malnourished and diseased. (+Disease, +Famine)
3) The dungeonhold lies in the center of a war zone. (+Overrun, +Intrigue)
4) The dungeonhold is stagnant, its populace enthralled by a neighbor. (+Reprisals, +Strife, -Hunger)
5) The dungeonhold is largely defenseless, with no militia, no walls, no armory, and a tumbledown keep.
6) The dungeonhold is an eldritch tear in the fabric of reality, attracting unusual and fearsome monsters. (+Adventurers, +Overrun)
Does the city in question lie adjacent to a horrible dungeon? If no, then this city is a hardhold, a place where the threat at issue is overland combat. A hardhold has:
1) Up to a thousand households.
2) Trade in cash crops, fine crafts, and services. (+Idle)
3) A thick stone keep, high walls, and parapets.
4) An armory of martial weapons and countless missles.
5) A standing army of around a dozen bastard knights, five dozen soldiers, and up to ten dozen conscripted irregulars.
6) Nonaggression pacts with all neighboring hardholds, and patronage over all neighboring dungeonholds.
Pick four from this list:
1) The hardhold is metropolitan, featuring a population up to ten thousand households, and three tiers of city walls. (+Anxiety)
2) The hardhold is a luminous city state. Up to a hundred noble families live within a massive fortified complex, supported by their servants. (+Intrigue, -Idle)
3) The hardhold has an famous magic academy, attracting students from far and wide. (+Strife)
4) The hardhold is an industrial leader, featuring a Damascene steel smelter, masterwork craftsmen, and even a skunkworks lab. (+Overrun)
5) The hardhold is nearly impervious to invasion, with high towers, ancient adamantium walls, and an immortal standing army equipped with masterwork arms. (+War)
6) The hardhold has favorable trade and cordial relations with its neighbors.
And two from this list:
1) The hardhold has entered into a period of decline. (+Idle, +Strife)
2) The hardhold has been condemned as decadent and blasphemous by a local religion (+Damned, +Reprisal)
3) The hardhold serves the bidding of an extradimensional terror. (+Overrun, +Curse)
4) The hardhold is on the verge of social revolution. (+Anxiety, +Intrigue)
5) The hardhold has largely illusory defenses.
6) The hardhold is surrounded by traitorous kingdoms, just waiting to strike. (+Intrigue, +Overrun, +Anxiety)
Tags (+something, -something else) have no specific mechanical value, but I would suggest you build fronts from them. Just as with AW, tags are binary and not cumulative. A kingdom with two +Strife ought to be identical to a kingdom with one +Strife.
+Adventurers: Powerful travellers come to the hold and stir things up for their personal glory.
+Anxiety: The populace are paranoid, and tend to flee from town and hoard whenever something comes up.
+Curse: There’s the stench of something ancient and foul coming from the ground and it won’t go away.
+Damned: The gods ignore the populace or see them as a tumor on the world.
+Disease: The populace have major health problems.
+Famine: The populace is always malnourished, weak, and committed to whatever ends to keep themselves alive that day.
+Hunger: The populace will do anything to eat.
+Idle: The populace aren’t exactly productive, and will return to their base impulses when work is slack.
+Intrigue: The elite have jealous rivals.
+Overrun: The hold is imminently seizable, and rivals do not delay to add the hold to their crown.
+Reprisals: A few plucky heroes have sworn vengance in the face of their dehumanization by the populace.
+Strife: The populace is rife with internal conflicts which are bound to come to a head.
+War: The elite are a bellicose lot, always at war, even at the cost of imperial overreach.