"Wilderness" monster lairs (really "outdoor" monster lairs, since they can appear in inhabited as well as wilderness areas) have much in common with other location types in the sandbox. They're kind of like dungeons, and kind of like strongholds. Monsters can have lairs in dungeons. A stronghold is essentially the lair of its ruler or occupants. The Caves of Chaos is the quintessential monster lair in classic D&D, but it looks very much like a dungeon and plays very similarly to a stronghold, the difference being mainly one of aesthetics and the "personhood" of its inhabitants (i.e., whether or not it is socially acceptable to kill them). The Hall of the Fire Giant King is a monster lair but is also literally a stronghold.
Lairs look different depending on who lives there. A monster lair might just be a room in a dungeon. Outdoors, it could be a cave full of owlbears, which is very obviously a lair, or it could be a leprechaun's burrow, which is visually almost indistinguishable from a hobbit hole. Your character might be a hobbit. To them, that's just a home! Orcs sometimes live in villages, and an enclave of elves is probably like a village too, albeit with a different aesthetic and inhabitants. Giants and vampires and such live in castles. All sorts of monsters can inhabit deserted strongholds.
Despite their similarity to other locations, monster lairs serve their own gameplay purpose and satisfy a unique niche in the sandbox. They vary in complexity. The cave which is home to a small pack of dumb beasts is simpler than the ruin where a dragon slumbers, surrounded by a few dozen sycophantic humanoid worshipers, which in turn is simpler than the underground city inhabited by hundreds of highly intelligent, organized Drow.
In my own musings on the subject, I argue that monster lairs of lesser or greater complexity serve as "stepping stones" from one level or tier of gameplay to the next. Using my B1 sandbox as an example, the owlbear den offers something for the players to do after they finish exploring Quasqueton, but before they're prepared to infiltrate or lay siege to Fayette's Hold. The ogre den similarly offers a transition from that stronghold - with just a meagre garrison and a relatively less powerful fighter ruling it - to the strongholds of Lambrecht and Blachefleur, the Evil wizard and cleric who hold dominion over the town of Timbershore. If there were also a lair of, say, 300 orcs out there in the wilderness, that would likewise offer some "endgame" content for the players, perhaps after they've liberated the town from its sinister rulers.
Keeping in mind the relative complexity and challenge level of your monster lairs, you can make an educated guess as to which will be easiest to detail and which your players are likely to explore first, which will in turn inform the sequence you should follow when developing these locations. Going by complexity alone, I might first detail the giant eagle nest, Jinglepuff's Burrow, and the owlbear den first, for example.
You can also anticipate your players' likely actions based on the locations' proximity to inhabited lands. Going by this metric, I might first choose to detail any monster lairs found in Timbershore, then take on Zerelda's Camp (yes, a camp of adventurer NPCs is a "monster lair") and the ogre den because they are close to inhabited lands and relatively easy to get to. The giant eagle nest, Jinglepuff's Burrow, and the owlbear den are comparatively remote, so they could wait for later.
In reality, none of these locations should take long to detail, and any of them might become relevant sooner or later depending on the players' interests, so they all end up being developed during the same "phase" of my process. I just kind of jump around from one to the other depending on whichever one interests me next.
The owlbear den seemed really straightforward, so I knocked that out right away. I had never keyed a leprechaun burrow before, so I did that next because it seemed fun. There was also a monster lair in Timbershore which really caught me by surprise (and which I won't spoil here), and was so delightful that I simply had to do it next. Have fun with it! Keep the momentum going however you see fit.
As usual, I will start with a minimalist sketch of the location. For monster lairs, this includes what type of monsters live there, who their leader is (if they have one), and how the monsters as a group react to adventurers (or the outside world more generally).
Are the bandits led by a fighter? A wizard? A cleric? Are they actively riding around the countryside, killing, looting, and burning, or are they simply threatening and demanding tribute? They might be Robinhood types, stealing from the rich to give to the needy. Are the orcs causing problems, or just keeping to themselves? Are the elves reclusive, or interested in trading with the human population? Just because the "monsters" are not hostile "enemies" doesn't mean the place where they live isn't worth detailing!
Next, I'll hammer out specifics, like the number of monsters present and what treasures they possess. If you're using something like AD&D, the Monster Manual will simply tell you these things, which is awesome (keep in mind that the actual number of monsters appearing compared to the total possible number will affect the amount of treasure they have). X number of goblins appear in dungeons, Y wandering the wilderness, and Z in their wilderness lair. If they're in their lair, they have so and so leaders and a such and such percent chance to have this or these monsters as guards. It's great stuff.
You might be using some other resource depending on your system of choice, in which case you might have to fill in the specifics with your imagination. The thorough procedural structure of AD&D is one of the many reasons I find myself coming back to it when wanting to run a game.
Honestly, if you're running something like modern D&D, the AD&D numbers work just fine. Even if you're running 5e, try having a bandit camp with 200 bandits in it. That will throw your players for a nasty loop when they hear about the bandits plaguing travelers on the road and assume it's a quest hook for 1st level characters with a carefully balanced combat encounter designed for them to easily defeat, only to find that they need a small army to root the bandits out. The number of monsters suggested by AD&D is less about adhering to some esoteric underlying math and more about creating a lifelike world.
Once you know how many monsters there are and how much treasure they have, you will need to figure out how that's all distributed throughout the lair and convert it into a table-ready key. For small-scale lairs, I think it's quite easy. I use a variation of the same "chunking" method outlined in my post on developing dungeons. Let's revisit this table from the AD&D DMG:
Since there are normally 12 "empty" rooms per three "monster and treasure" rooms, my smallest lair needs only four "empty" rooms. There is about a 67% chance of there being another room with just monsters, and about a 33% that there is a "special" room, a trick or trap room, and a treasure room, respectively. That means your smallest monster lair is most likely going to have about seven rooms (four "empty", one with the primary inhabitant and its treasure hoard, probably one with another monster, and probably at least one special, trick/trap, or treasure room).
This works pretty well for a single leprechaun's burrow or an owlbear den with just a mated pair and their cubs. If the lair contains 300 orcs, you'll obviously want to adjust it up so that there's room to breathe. You also don't need to take it too literally - just because there's only two "monster" rooms doesn't mean those are the only two rooms with monsters in them. There is probably an ogre monitoring the room with the hidden pit trap and another standing guard by the treasure den. This is where they live. Spread them out!
You will also want to loosely interpret the results, since this isn't a dungeon. The number of "monster" rooms isn't actually telling you how many monsters are there, since the Monster Manual (or whatever is available in your system) is probably providing that information. Those are just the rooms where the monsters congregate (i.e. where they eat or sleep).
A "trick/trap" room isn't going to feature the same sorts of tricks and traps you'd find in a Mythic Underworld-style dungeon, but rather whatever sorts of devices the monsters in question might employ in their home, depending on the type of home they keep. These might be proper traps or simple obstacles, fortifications, wards, hazards, etc. Kobolds will set traps in their lair, but owlbears won't. A "trap" in an owlbear lair is going to look like something different. Similarly, the "special" room in the owlbear's lair might be a forgotten druid's shrine in the back of the den, accessible via a narrow tunnel, which offers some boon entirely unrelated to the owlbears themselves.
All this method is doing is providing the number of rooms and the proportion of gameplay features to include. For example, let's say I roll some dice and determine that, in addition to the requisite four empty rooms and the room where Jinglepuff is found with his treasure, his lair also contains an additional "monster only" room.
Since Jinglepuff is the only leprechaun who lives here, and the Monster Manual doesn't suggest that leprechauns keep other monsters in their lair, I refer to my indexing of AD&D 2e monsters by level. According to that, leprechauns are a 5th level monster, so I go looking for something comparable that might reasonably be found there as well. Blink dogs are also 5th level monsters, and are associated with fey creatures, so I might decide that Jinglepuff keeps a mated pair and their litter of pups as pets (great for capturing and selling into slavery).
If I were to have the same rooms in my ogre den, however, I might say that the "monster only" room is just where the majority of the ogre rabble congregate to eat and sleep, while the "monster and treasure" room is where the chieftain and his favored consorts and bodyguards dwell. This is because the ogre lair contains more than a dozen ogres, while the leprechaun lair has just one leprechaun. In the former example, I'm spreading out a greater number of monsters across multiple rooms. In the latter example, I'm bolstering a single monster's numbers with additional pets and guardians which make sense for that monster to keep.
For a lair of 300 orcs, I could do a full 20-room chunk, with huge garrisons of orcs living in each of the "monster only" rooms, and the chief and sub-chiefs (or whatever) making their own individual "lairs" in the "monster and treasure" rooms. That's still 60 orcs in each room (or, more accurately, 60 orcs spread out across the rooms each group is responsible for protecting), so I might make it a lair with 40 or 60 keyed areas - as I said, these larger lairs can become very complex!
This also prompts me to consider turning each of the sub-chiefs into their own factions within the larger orc band, since each has its own mini "lair" within the greater lair. This allows for more social gameplay and for turning one faction against the other to start an internecine war between them, not all that dissimilar from the Caves of Chaos. Might I suggest using opposing reaction rolls to determine how the different monster groups feel about one another?
Remember that just as strongholds and settlements assert their dominion via patrols, monsters will control their territory as well. Put some wandering monsters from the lair on your outdoor encounter tables. When monsters are found in a given area of the lair, note if who or what is there differs by time of day. If one cave is where the owlbears sleep, they're probably not there at all times. Perhaps one goes out to hunt for part of the day, while another stays behind to watch the cubs. Orcs hate sunlight, so you probably don't want to raid their lair during the day when everyone is home. If you go at night, some will be out hunting, which will make the raid that much easier.
Many of the same principles you might keep in mind when designing a dungeon apply to designing a monster lair. Jacquays it. Create a wandering monster table. Make sure the "empty" rooms still have interactable elements. If possible, include something to talk to, something to kill, something to be killed by, and a secret to find.
You'll want the place to feel like what it's supposed to be - a place where monsters live. This is not the Mythic Underworld, impossibly old and inscrutable, with weird rules of its own, where the ancient and alien nature of the place can explain away a lot of the weirdness in layout or features. If your dungeon is filled with undead or fiends or elementals, you probably don't need to worry much about dungeon ecology, but a monster lair is usually home to a type of monster which is much more grounded in the physical world and its requirements - humanoids and beasts that need to eat, drink, sleep, procreate, raise young, go out and hunt, entertain themselves, make themselves comfortable, and the like.
Just as dungeon history informed the specific way in which I stocked my hypothetical dungeons in my previous post, the nature of the monsters that dwell in the lair (and the nature of the lair they dwell in) will inform the way in which I stock their lair. Elves will use magic and warp natural features to suit their needs, dwarves will use shifting stone and have lots of room for crafting, and halflings will keep cozy lairs with full larders. Orcs will decorate the place with the skulls of their enemies, kobolds will employ lots of traps, and cackling will echo through the gnolls' warrens.
Another key element is to ensure the lair suits the monster's strengths. This is probably less so the case in a dungeon, where the monster is more likely there by happenstance, and some other creature originally designed the space for their own ends. The monster chose its outdoor lair for a reason, or modified it to suit its needs. Giant spiders will carpet the floor with webbing to detect prey entering. Fire giants will carve channels for molten lava to form moats. Black dragons will flood some portion of their lair and keep their treasure on the far side of a submerged tunnel. A beholder carves tunnels using its disintegration ray, and it can levitate, so it isn't creating its lair to be easily navigable by pitiful grounded bipeds.
Not all lairs are dungeon-esque. An informal camp home to adventurers, bandits, berserkers, or the like it not going to play like a dungeon crawl at all, nor is a giant eagle nest situated in the branches of a tree atop a tall bluff. These are much simpler, and you can probably imagine easily enough what the place looks like once you have the specifics figured out.
Monster lairs are excellent sandbox fodder, which is great, because you'll probably have a good amount of them, depending on the method you use to stock the sandbox. I determine the number of monster lairs based on the terrain. They are less common in grasslands and desert, but more common in swamps and mountains. If my sandbox is in a more "rugged" "untamed" region, there will be more monster lairs.
They vary in complexity, but are not overly complex until you get to the huge humanoid warrens and villages. At the lower end of complexity, they're dungeonesque, offering turn-based exploration and heated skirmishes in narrow confines. These are not overly difficult to bring to fruition. At the higher end, they're akin to strongholds, forcing the player characters to accumulate power and bring real strength to bear to lay siege to them. These will require significantly more effort to design.
Because there are so many different types of monsters, and each monster will have its own unique version of a lair, they also offer a variety of thematic flavor which will keep your campaign interesting. Bear caves, elf villages, ruined giant strongholds, ankheg burrows, giant beehives, ghoulish graveyards, vampire castles - these are all lairs, and they're all wildly different because of who lives there.
Monster lairs are great because they affect the world around them. Most dungeons are kind of just there. The players will want to explore them because that's what the game is about, and because that's where the treasure is. Monster lairs also have treasure, but the game is also about dealing with monsters, and the lair is where you deal with them.
That doesn't necessarily mean killing them. You might visit the goblin lair because the goblins have a powerful shaman who can cast a spell you need. You might wish to recruit them to attack the "civilized" frontier fortress where the really good treasure is kept. Maybe the local ruler wants to incorporate the goblins into their territory, the goblins are on the fence, and you're being sent to negotiate terms. Maybe the goblins are ruled over by the neighboring ogres, and they ask you to deal with them.
Be open minded about your monster lairs, what the monsters want, how they affect the world, and how the powers that be feel about them. That will color the way in which you expect the players to interact with these locations. Unlike dungeons, which monsters inhabit almost incidentally, lairs are where monsters choose to live. Why have they chosen to live there? How have they made the place their own? How has their choice to live there affected their neighbors? What, if anything, is to be done about it?
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