Random encounters serve a few purposes.
First, they serve to make the world "feel" "alive" by establishing a facade of movement. NPCs move around and do stuff.
Second, they serve as a resource tax on time (and by extension, distance) which is the driving force behind the dungeon as "dive" - You have to decide when to come up for oxygen and or HP.
Third, they serve as an improv prompt for the DM. The encounter die said that there are 20 bears here, and the scenario die said that they're furious. Now the DM has to decide what they're furious about.
Fourth, they're combat! Combat is fun, in theory.
Here are the problems with random encounters:
First, I think there's an instinct on the part of most DMs to over-bestiary themselves in general, but ESPECIALLY on Wilderness Encounters. If you use online resources to roll against "Everything that might be in a temperate climate, plus everything else on a 5% chance" that feels inclusive and realistic but also generally means rolling against too many charts.
The solution here is twofold
1. Deliberately limit your bestiary to some degree. This helps establish a theme.
2. Do 99% of your rolling ahead of time. You can, while sitting at the table today, discover that there are 20 furious bears, and find out what treasure they're carrying, and decide what they want, and then record all of that and during the session just roll a d20, get a 15, and see that 15 is "The 20 Furious Bears Encounter"
Second, wilderness travel tends to happen on a much larger timescale, which raises some logistical issues since most resources are time-based. If you want to have the party go to a destination a month away, that's either a hundred encounters (and given that my party struggles to have two combats in a session, that means this journey will be a grueling slog taking years realtime) OR relatively few encounters per day.
Possible solutions here:
1. Wilderness encounters are easy and safe: which means they make a good "trial fight" where you debut enemies and tactics that would feel mean to spring without warning. They can also be an opportunity to drop potential hooks and narrative information.
2. Alternative stakes: Since the PCs are almost guaranteed to survive the encounter, put something else in the fight that's acceptable to lose. If there's a weak NPC (either a party member or just a random sad person that's being attacked when the PCs walk in) to protect, that can easily introduce stakes. Party resources like food, torches, horses, and soldiers are also a potential loss. The goal here is to imagine a fight where nobody died or was really in danger of death but the PCs were still concerned. (this is also good practice in general for TTRPGs and I'll explore it in future posts)
3. Go hard: Just calibrate your wilderness encounter to NEED roughly all their spells and HP. If they get all their spells and HP back after every wilderness encounter, just plan around that. Every fight in the wilderness is against a deadly foe. One pro to this approach is that the wilderness lends itself to larger monsters anyway- it's easy to imagine stumbling on a herd of mammoths or whatever, out on the plains. (It also dovetails nicely with solution #1: If the PCs have encountered a Dire Pyrophant on their way to the dungeon, and it knocked out half of Gorbo's HP with one hit, then they will know exactly what it means when they see the one guarding the Staff of Treachery.)
4. Dungeonesque: Maybe the journey is a month long, but it's actually 28 days of quiet grassland and 2 days going through Butcher's Forest, where they'll have their Surgeon-General-recommended 4 servings of kobold per day. In some ways it's the most elegant solution, but it requires some pretty strong rules about the world and breaks down over time; once the party understands that Butcher's Forest is an extremely dangerous place, what makes them choose to go through it again on future trips? Just how many wild Danger Zones are there? Are you placing quest hooks on the map specifically to encourage crossing Danger Zones?
As usual, in D&D, the answer is to mix and match in a ratio that works for you. In my next post I'll start drafting my random encounter system for Unsettled, my ongoing 5e campaign.
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