Secret Santicore: Random Wilderness Stronghold

So there’s this thing. Perfect excuse to write something interesting and get something interesting; Secret Santa, but with D&D material.

The prompt I got:

“I would like alternative randomly generated strongholds to encounter in wilderness hexcrawls (or for setting design).

Like the ones in The Underworld & Wilderness Adventures, pages 15 an 16.

This would require some way to determine who the stronghold ruler is (class or monster type), who or what their primary henchmen or allies are, and what other soldiers or resources they can call on, and what kind of stronghold they have.”

All right, let’s do this. Roll once on each of the following tables (except the Weirdness table, you can skip that one if you want the location to be less than completely insane).

Stronghold Ruler:

01. Noble of nearest kingdom/empire/nation-state/whatever.
02. Noble of furthest away kingdom/empire/nation-state/whatever.
03. Former adventurer, high level, settling down to rule his tiny domain (Roll 1d4: 1 Fighter, 2 Rogue, 3 Cleric, 4 Class of the last character you played)
04. Insane wizard.
05. Priest of pacifist religion. Will try to avoid fighting at all costs.
06. High Priest of All that is Evil.
07. Young child. Roll a random die: even, the child is ruling on his/her own, odd, roll again on this table to see who the reagent is.
08. Warlord. Possibly a Viking.
09. Democracy of some kind.
10. Huge-ass dragon. The throne room has an open roof so it can fly in and out.
11. Lich.
12. Abbott or other head of a militant religious order based in the stronghold.
13. Mercenary commander. This is the headquarters of his private army.
14. Strange man speaking a different language, worshiped as a god by all who live in the area.
15. Necromancer.
16. King of Ogres.
17. Vampire Lord.
18. Queen of Fae, or some other weird LSD-trip creature.
19. Mad scientist/artificer.
20. Roll twice more on this table. The first roll you get is the visible ruler of the stronghold, who is secretly controlled by the guy from your second roll. Man-behind-the-man situation.

Type of Stronghold:

01. Motte-and-bailey. Wood keep on a manmade hill, surrounded by a wooden palisade and a ditch. Nothing special.
02. Lonely tower.
03. Stone keep. Very defensible, stone outer wall, outbuildings, maybe a small town surrounding it.
04. Underground complex. Topside entrance is small and nondescript, like a wood hut or something.
05. Concentric castle. Might have a keep, might not; the main point of a concentric castle is the two sets of walls. The inner wall is high and thick, with turrets at even intervals; the outer wall is just as thick, but lower. The idea is that archers on the inner wall can still hit people approaching the outer wall, so you’ve got two sets of archers shooting at everyone. God help you if you get stuck between the two walls–they call that area the killing field, and the name is apt.
06. Stronghold is just a bunch of normal buildings, but the crazy powerful magic wards serve to keep most enemies away.
07. Island. Either in the middle of a river or a lake or something. Due to the walls and cliffs, the only way to access it is by one dock, which is heavily defended.
08. Pyramid. Built by an ancient civilization, or by the current occupants? You decide.
09. Fortified monastery.
10. Viking-style hall.
11. Spiky citadel of doom. Cliched Gothic-evil stuff everywhere.
12. Hollowed-out carcass of a giant animal.
13. Naturally defensible; cliff, pass through the mountains, whatever. Existing fortifications are minimal, and mostly serve as shelter; it’s hard to improve on a natural position this good.
14. Simple wooden palisade, with temporary shelter set up inside.
15. Star fort (outer walls arranged in a star-like formation, to allow different walls to cover each other and prevent enemy sappers from undermining the wall). These forts existed during the age of gunpowder, and were designed for that sort of warfare; thus, if your world has gunpowder, the guys manning this fort most likely have cannons.
16. Cathedral. Most defenses are of the holy variety–things to drive back evil spirits and whatnot. Some minor physical fortifications.
17. Fortified village. Earth-and-wood wall surrounds the place, gates are locked at night against that which lurks in the dark.
18. Couple of blockhouses connected by stone walls. Blockhouses are armed with artillery of some kind–catapults, cannons, ballista, whatever.
19. Crazy long wall blocking off access to some geographic feature (forest, mountain, country, etc).
20. Fortified wayhouse, with rooms and food.

Stronghold Weirdness:
Roll on this chart to add weirdness. For a low-magic setting, maybe 10% of the time; for a weirder setting, maybe 80% of the time. You choose whether to use this chart or not.

01. Made out of some incongruous material–ice, coral, glass, solid cloud, living flesh, etc.
02. Only exists at night.
03. Suffused with an unearthly light. All who view the stronghold must make a will save or become entranced by the light.
04. Fae-touched. The rules of reality here follow storybook logic rather than physics.
05. Everyone in the stronghold is conspiring against everyone else.
06. Home to vast, cursed riches.
07. Stronghold is conscious.
08. Mobile.
09. Every single corridor is trapped.
10. Everything implied by the rolls on all the other tables is the opposite of how it should be (heavy defenses are useless, kind priest is Lord High Evil, insane wizard is actually a decent guy, that sort of thing).
11. Normally deadly enemies (elves and orcs, for example) coexist (almost) peacefully in this stronghold.
12. Peaceful-happy-village-with-a-disturbing-secret-type-thing.
13. Someone here believes that the approach of the party fulfills some prophecy. Reacts with (roll a random die) even, hostility, odd, welcome.
14. Everyone except one guy is actually high-level assassins in disguise, waiting for the perfect moment to strike.
15. The gods walk these empty halls.
16. Terrorized by some sinister creature/serial killer.
17. Surrounded by perpetual storm.
18. Actually a disguised gateway into Hell.
19. Building materials taken from a petrified giant; the spirit of the giant is still kind of pissed about that, and hangs around haunting people.
20. Cursed. All who step within shall come to a deeply disturbing end.

Type of Minion:

Bear in mind that whatever is rolled on this table will most likely not be the only type of minion that the ruler of the stronghold will have. For example, a necromancer will probably have undead minions lying around, even if that is not rolled on this table. Use your own judgement. Why does the necromancer have standard chainmail-wearing grunts as the bulk of his forces? Is he trying to hide his black magic from his men? Or are the undead his elite hit squad? Something like that, you can figure it out I’m sure.

01. Chainmail-wearing, shortsword-slinging, crossbow-shooting mooks.
02. Gargoyles, golems, and other living statuary.
03. Undead. Skeletons, zombies, vampire spawn, whatever.
04. Samurai.
05. Monks, of the pacifist, scribing-illuminated-texts kind.
06. Monks, of the punchy kind.
07. Fanatically devoted cultists.
08. Bunch of mind-controlled dudes.
09. Minotaurs, satyrs, and other beastmen.
10. Cannibalistic mutants.
11. Anachronistically professional soldiers who take full advantage of magic and operate like modern day special forces.
12. Orcs, goblins, hobgoblins, or some other sort of generic evil humanoid.
13. Lizardfolk.
14. Appear to be ordinary, if expressionless humans, but if threatened will reveal they are actually automatons.
15. Knights. Lots of guys in heavy plate, with huge weapons.
16. Incongruously advanced troops–arquebusiers, or musketeers, or riflemen or something.
17. Ghosts.
18. Intelligent animals.
19. Animated furniture.
20. Identical copies of the fortress ruler, controlled by him directly.

Why Is There A Stronghold Here In The First Place

01. Mines. Gold, probably, but could be coal or iron or some other resource. Dunno why anyone would build a castle in the middle of the goddamn wilderness for anything less than gold, though.
02. Kingdom/empire/protectorate/nation-state is trying to expand its borders. Ruler of the stronghold was given his authority by nearest civilized nation.
03. Old megadungeon-style ruins, being excavated and explored by the stronghold residents; stronghold built to keep other adventurers away/defend against things coming out of the ruins.
04. Trade route. Caravans come through here all the time. Large transitory population around the castle, with all the criminal shenanigans that implies.
05. Every hundred years, on the full moon of the third month, a greater demon appears in this spot and will truthfully answer one question posed to it. The ruler of the stronghold is determined to be that questioner.
06. Religious location of some significance (death/burial place of a martyr or saint, location of an ascension to godhood, whatever).
07. No particular reason why the stronghold is here–the guy who built it just wanted a place to settle down, and chose the nearest spot with a decent view.
08. Monsters! Stronghold constructed as a bastion against the goblin/skeleton/vampire/highlander hordes.
09. Built by an insane wizard. No logical reason needed. Stronghold is built in the weirdest location possible, given local terrain.
10. Important historical artifact was once kept here; artifact is still here, but no one cares about it anymore.
11. Was once the capitol of a vast empire, until the earthquake. The new tenants just moved in.
12. Some menace from underground (drow, goblins, demons, giant spiders, whatever) emerged from this location to assault the world of light. Stronghold was originally built over the tunnel entrance, to keep the menace contained.
13. Stronghold was built in the shape of an enormous magical rune by a past archmage, for purposes unknown.
14. Miscommunication led to the stronghold being built here, instead of somewhere important.
15. The most fertile land in a hundred miles can be found in the shadow of this stronghold. Fortress was built to control the land. Roll 1d4; land is 1 Still being farmed, 2 Completely overgrown, 3 Still farmed but maltreated and lifeless, 4 A blasted wasteland.
16. Outpost of some previously-unknown kingdom.
17. Stronghold originally built by refugees, fleeing some long-ago disaster.
18. Extremely militant organization is using the area as a staging ground to plan its invasion of everywhere.
19. Stronghold is an obvious ruin, rebuilt by the current occupants.
20. Prophet had a dream that told him to build the stronghold here.

Other Details:

There is a 20% chance that the stronghold is still under construction or being added to in some way.

Most people in a stronghold in the middle of the wilderness will demand a toll for passing through their lands. Call it 500-1500gp. 90% of strongholds will demand such a toll (if the 90% is rolled and a clerical type is in charge, the toll will instead be a tithe of 10% of all gold/gems owned by the players).

Wizardly types may attempt to control parties that cross their lands with geas spells and the like, and send them after magical artifacts.