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Building Wilderness Journeys

The Lord of the Rings (and to a lesser extent the Hobbit) is foundational source material for tabletop roleplaying, and its primary quest is getting an evil ring from Bag End to Mount Doom. That’s a campaign, not an individual adventure, and some of the individual adventures in the D&D version of that story are a dungeon crawl – Mines of Moria and Shelob’s Lair for sure, and arguably Osgiliath (if we’re using the movie version) and Cirith Ungol (if we’re using the video game version) – and some of them are possibly mysteries, although those mainly come up in Gandalf and Aragorn’s branches of the story (the intrigues with Grima Wormtongue and Denethor were more like social encounters than full-on mysteries, but if you want Lord of the Rings to be a campaign and not a book, turning these pivotal moments into full-on mystery adventures is a very defensible choice).
There’s several adventures in the Lord of the Rings which are just a microcosm of the greater campaign, though. The adventure of going from the Shire to Bree, and then from Bree to Rivendell, are just about getting through locations. Get through the Old Forest. Get through the Barrow Downs. Get through Midgewater Marsh. Get through the Trollshaws. Most of Frodo and Sam’s journey following the breaking of the Fellowship at Amon Hen are similar: Get through Emin Muil. Get through the Dead Marsh. Get through Ithilien. Get through Gorgoroth.

Why Not Dungeon Crawls?

You can try to run these as dungeon crawls. Rather than each room being twenty feet down from the next, you can instead have the party follow different trails and pathways, with twenty minutes of walking between each encounter. This space makes it easy to justify having significantly more variety in enemies. If your first encounter is a pack of goblins, and then an ogre, and then a displacer moose, the answer to “what are all these things doing here” can just be “they all have lairs close-ish to one another.” However, that same distance means that the presence of factions is not felt nearly as strongly. With so much distance between them, and with the goal being to get from point A to point B rather than to explore and find treasure and/or reduce enemy troop counts, there’s not much incentive to interact with enemies in the area in the first place. The lack of levels means that a lot of layout tricks that make dungeons more interesting aren’t available. You can use the same tricks on discrete sections of a dungeon crawl that aren’t actually vertically stacked levels, like having a number of different forest camps networked together by trails and pathways, each camp a different “level” of the dungeon, but few of those (including the “network of camps” example) are effective when there’s expected to be half a mile or more of distance between each encounter to begin with.
Furthermore, while some of these locations are certainly labyrinthine – the Old Forest, Emin Muil – others are quite straightforward – Golgoroth, the Barrow Downs. Golgoroth is actually quite flat and surrounded by mountain ranges some of which are much closer than others, and occasionally dotted by very large landmarks like Mount Doom and Barad Dur. It’s really easy to remain oriented there, which means even if there are branches and loops, there isn’t really any incentive not to just wander off directly towards your goal and ignore anything that comes up on the side. If the whole point is to get from Cirith Ungol to Mount Doom, why would we even consider wandering several miles off of the most direct route just to see if there’s anything interesting out there? Especially when it’s just as likely to be an orc warcamp with nothing but pig iron swords they’re trying to stick in us as it is to be some kind of actually useful treasure.
Dungeon crawls rarely work well when the goal is simply to get from point A to point B without any compelling side quests at all, and especially not when it’s always or almost always clear where point B is in relation to the party’s current location. Dungeon crawls are about exploration, and any goal that encourages you not to deviate from the path is not suited to a dungeon crawl. The same basic principle applies to hex crawls (which we’ll talk about in the Art of Campaigns), so using them is a non-starter, too.

What Is A Wilderness Journey?

A wilderness journey is essentially a string of random encounters until the encounter table has been thinned out enough to permit passage, punctuated by decisions about where to go next. Each area in a wilderness journey has a random encounter table attached to it. The bigger the table, the more encounters before getting through it, either because the area is physically larger or because it is more dense with enemies. Players roll on the random encounter table and deal with whatever encounter comes up on the table. Then the GM crosses that encounter off of the table (there are rarely multiple encounters in the same random encounter slot in a wilderness journey table the way there are in dungeons) and the players roll again. If they roll a result they’ve already had and crossed off, they ignore it, and go to the next result down or up, whichever direction is closest to their destination. So, for example, if their destination is encounter 1, the players roll a 5, but 5 is already completed, they instead go to encounter 4. If 4 is also already completed, they’ll go down to encounter 3 instead, and so on, until they arrive at an encounter that hasn’t been completed yet.
If you want to guarantee certain encounters happen before players leave an area, you can have the destination be off the chart. For example, if the destination is encounter 0, then the only way to reach it is to complete encounter 1, then roll another 1 and slide down to encounter 0. You can also have encounter -1 or -2 or however many encounters you need to guarantee before the party leaves. Use this technique sparingly, however. If you use it too much, the party is likely to hit every single encounter in the area by the time they get through encounters 0 through -6 and finally reach the actual exit.
All encounters have a chance of happening at any point in the journey. Don’t make the mistake of thinking of encounters near the goal as being physically closer to that goal. If players are heading from the Misty Mountains (encounter 0) to Erebor (encounter 13) they might hit encounter 12, then encounter 1, then encounter 12 again, which gets them to Erebor. This does not mean that they got most of the way through Mirkwood, then got turned around and walked most of the way back, and then turned around back in the right direction and walked all the way through Mirkwood again. It means that whatever spiders or bats or goblins were in encounter 12 happened to be the first thing they ran into, and then whatever else was encounter 1 was the second thing they ran into, and then they got out of Mirkwood to Erebor without ever getting turned around at all.
Likewise, mandatory encounters should not be things that are immediately adjacent to the goal, because they may come up at any time during the journey. If you want your goal to have one or more layers of defense immediately outside of it, bake those layers of defense directly into the goal encounter. Do not make each layer a separate mandatory encounter. A good example of a mandatory encounter is the Elven city in Mirkwood. Even after leaving the city, the party isn’t out of Mirkwood and may encounter more spiders or goblins or whatever before reaching Erebor (although in the book/movies they didn’t). A bad example of a mandatory encounter is Laketown. Laketown is between Mirkwood and Erebor. Once you get to Laketown, you are not going to have another spider encounter. Instead, Laketown is just a part of the Erebor encounter. In this example specifically, the Erebor “encounter” is probably a complete adventure unto itself, since it’s actually the end of the journey, and unless you’re delivering the mail, the end of the journey is probably going to be a separate adventure in which you do the thing you set out to do. You reach the end of your journey and you have a dungeon crawl, or a mass combat, or maybe a mystery. On the other hand, Lord of the Rings actually is about delivering the mail, and once you reach Mount Doom all you need to do is make a Will save to drop off the ring and you’re done.
Assuming exits are just barely off the chart, players will find, on average, a little over half of the total encounters. The more encounters you add above the chart before players can reach their goal (i.e. if Erebor is encounter 14 or even 15 instead of 13, thus requiring more mandatory encounters before you can reach Erebor) the more likely they are to clear a larger total number of encounters and the more likely it is that higher encounters specifically will be cleared. If their goal is low on the chart instead of high, the reverse is true: They are more likely to see encounters lower on the chart, and that likelihood increases the further off the chart you push the goal encounter. The reason for this is because, when they roll an already cleared encounter, they are pushed towards their goal and into any remaining encounters still near their goal.

Multiple Exits and Intersecting Encounter Tables

Some areas might have multiple exits. For example, Mirkwood has the Misty Mountains on one end and Erebor on the other (I’m simplifying the geography a bit for example purposes – just roll with it). In this case you’ll want one exit off the chart in one direction and the other off the chart in the opposite direction. For example, say Mirkwood, being a rather large area, is a d12 region. The Misty Mountains would be encounter 0, and Erebor would be encounter 13. If the Misty Mountains were encounter 1, then a party might roll a 1 after completing several other encounters and find themselves back at the Misty Mountains. This feels like the party isn’t making any progress. If the Misty Mountains is encounter 0, then when the party rolls a 1 they will get an encounter appropriate to any point within Mirkwood.
Sometimes an area needs three or more different exits. Continuing our Mirkwood example, let’s say we need a southern exit that leads out towards southern Mirkwood, where you’ll need to go if you want to reach Dol Guldur or head past it towards Lorien. The branch point from the standard Mirkwood path to the southern route would be somewhere between the Misty Mountains and Erebor, let’s say encounter 6. In this case, if the party rolls an encounter they’ve already had in slots 1-5, they’ll slide upwards towards encounter 6, but if they roll an encounter they’ve already had in slots 7-12, they’ll slide downward, still towards encounter 6. If the party is heading towards Erebor or the Misty Mountains and rolls a 6, they’ll encounter the route south and (unless they for some reason want to take a major detour) ignore it.
Sometimes you want these middle of the way areas to be off the charts as well. Maybe you want all of Mirkwood to be a single area with a single encounter table instead of having the northern and southern Mirkwood tables that intersect with one another, but you can’t put Dol Guldur at encounter 6 or else anyone heading from the Misty Mountains to Erebor or vice-versa could end up way off course. In this case, just have the encounter to the side. Just like encounters that are above or below the encounter table, encounters to the side can never be encountered by a natural die roll, so if Dol Guldur is encounter 6B, then the only way to reach it is if you’re heading there, you roll a 6 to receive encounter 6A, and you’ve already cleared encounter 6A, so you get shunted in the direction of your goal – in this case, sideways, to encounter 6B, Dol Guldur. If you’re headed from the Misty Mountains to Erebor and roll encounter 6A after you’ve already cleared it, you’ll be shunted upwards to encounter 7 instead, and never see Dol Guldur.
You might be tempted to have your wilderness areas be a full-on grid at this point, but at that point you are better off making a hex crawl (and your plot hook should be more exploration oriented than traversal oriented).

An Example of a Journey Through Multiple Areas

This blurs the line between adventure and campaign, since a wilderness journey through multiple areas could plausibly be a small campaign unto itself. The same could be said of a sufficiently large dungeon or a sufficiently complex mystery, though, so we’re in good company. Switching from our Hobbit-based Mirkwood example to a Lord of the Rings based one, the journey from Rivendell to Emin Muil had a total of three different potential routes, and picking which one to take was a minor plot point in the movies and especially the books. The most straightforward route was to go south through Eregion, then down into Dunland, through the Gap of Rohan, and out into the Wold towards Emin Muil. This would be four separate areas: Eregion, Dunland, the Gap, and the Wold.
Even within this one route there are alternatives – instead of riding out to the Wold (patrolled heavily by Sauron and Saruman’s forces) you might instead pass through Fangorn (particularly if you’re on good terms with the ents, which the Fellowship wasn’t particularly, but D&D parties might want to take their chances negotiating with tree people rather than fighting orcs) and then take the Anduin down to Emin Muil. Boromir suggested ignoring Emin Muil altogether and passing from the Gap straight through Rohan and into Gondor. Lacking knowledge that Rohan was currently being pillaged by uruk-hai in a precursor to a full-scale invasion, this plan was a pretty solid choice except for requiring passage through the Gap of Rohan where Isengard was situated.
Gandalf favored crossing the Misty Mountains over to the Gladden Fields, then following the edge of the mountains down into Lorien, where they would take the Anduin through to Emin Muil. The advantage of this plan was the relative lack of Sauron’s vassals or allies in the region. However, the party found the crossing of the Misty Mountains too difficult (in the movies Saruman is specifically impeding their progress, and in the books it is more ambiguous but it is stated that the mountains themselves seem to be resisting their efforts to cross, and the severe weather lets up once they turn back), so they settled on the third plan.
Gimli’s plan was to head south through Eregion just like Borimir’s, but rather than continue to Dunland, Gimli would have turned to the Mines of Moria to get through the Misty Mountains. From there, they could head through Lorien and onto the Anduin towards Emin Muil just as in Gandalf’s plan. Moria was contested territory between the dwarves and the goblins. Gimli believed that the dwarves would be secure in their holdings, especially near the surface where they’d begun their reclamation efforts, but Gandalf feared that bringing the ring there would draw the attention of the balrog. Things turned out to be worse than even Gandalf feared. The dwarves were already defeated and the Mines were entirely held by the balrog, an ally of Sauron.
Is this Lord of the Rings minutia or a detailed example of three different potential chains of wilderness journey adventures? It’s both, of course, and that’s how you know a wilderness journey chain is working. These are exactly the kinds of choices you want players to be facing when planning a journey through the wilderness. Having lots of different wilderness areas, some intersecting with others, allows players to sit down and figure out the game mechanics of their journey without breaking character, and that’s mechanics at their finest (Boromir even has a specific roleplay reason to favor the Gap of Rohan route despite the risks of taking the ring so close to Isengard).
If your plot hook is going to be a wilderness journey through multiple areas, split up all the territory of your campaign world between point A and point B into regions, give players a brief overview of what they know about each region (the information doesn’t have to be accurate – the Fellowship didn’t know the dwarves’ attempt to reclaim Moria had failed, nor did they know how desperate Rohan’s situation was), and ask them to plot a route. It’s possible that they’ll end up taking a route you didn’t plan on (what if we take the ring west to the Grey Havens and commission a ship down to Gondor, then head into Mordor from there?), so it may be wise to plan out every region that immediately neighbors the starting region, giving you time to add in any regions the players plan to pass through that you didn’t think would be necessary.
If you’re really dedicated, you might think it’s a good idea to fill in encounter tables for crossing every single region in your game world, and for a certain campaign premise, that can even be a good idea. If you’re the D&D Pony Express, then you probably will end up criss-crossing all over the world map with a wilderness journey setup being appropriate each time. However, if you’re drawn to this option mainly because you’d like to have your players explore all across your world, look instead to hex crawls and wilderness campaigns over in the Art of Campaigns.