Running an interesting wilderness travel session is hard. Part of that is because there are different reasons for that session. Do you just want to get from point A to B to continue the story? Or is there something in the wilderness you need to find?

One of the odder random wilderness encounters in a published adventure was a multi-room monster lair. The problem? It occurs as you’re chasing a thief. Why are you abandoning the search to explore the lair? (Answer: You don’t. It’s a poor encounter).

Points of interest to explore and NPCs giving side-quests are great when you’re not on a time-dependent quest. This disconnect also occurs in open world computer games, to greater and lesser degrees.

If you’re on a goal-centred expedition, the encounters you experience should provide challenges that disrupt the journey, and potentially mean you have fewer resources when you reach your destination. Of course, enabling resource management is not one of D&D 5E’s strengths.

If the wilderness travel is more on the “what’s out there?” side of things, then you want more of the points of interest to explore.

An interesting side point is that when arriving at the destination ends the adventure is a very different matter to when arriving at the destination starts a major part of the adventure. The emphasis on travel changes.

“Deliver the medicine to the doctor in the next town” works differently to “Go to the dungeon a week away and find the medicine in its depths”. In the first, once you arrive in town, the adventure ends. The adventure is the travel. In the second, the travel is one more challenge in an entire suite of challenges.

Random encounters are the backbone of how most* DMs run wilderness encounters. The traditional way is for the group to encounter a random number of monsters. But honestly, I want more. (* For a given value of most.)

For 10-year-old me, having a random encounter with monsters to kill was great. For 50-year-old me, I still love combat, but I want a wider range of ways to approach the encounter. What do the monsters want? What are they doing?

Many recent products tell you exactly what the monsters are doing. But they’re designed as one-use encounters. Which aren’t that great when you’re doing a lot of wilderness travel in that area.

The purpose of the randomness of encounters is to help me with prompts to flesh out the encounter. If an encounter with 4 ogres then has me roll a d4 to determine that the ogres are:

1. Chasing an escaped Prisoner
2. Looking for food
3. Transporting tribute to a local warlord
4. Seeking to hire out as mercenaries.

Then that gives more variability; and permits the players to react in ways that aren’t always “kill the ogres!”

I’ve been playing with Cubicle 7’s Uncharted Journeys of late, and one approach it uses is to limit the use of rests. Every journey takes place over the course of a single “long rest” period, and you can only take one short rest – and if you do, there’s an extra encounter in the journey. This brings a greater tension to the travel, which is great for travel that is purposeful – that is, with an intended destination, rather than just exploring to see what is out there.

The problems with its approach come from not having enough encounters with monsters, an over-reliance on exhaustion rules, and an incredibly bad DC-setting system. But the good about it – which includes a lot of encounter types not found in regular products, an emphasis on skill use, and a frankly inspiring look at wilderness encounters, makes me want to explore it more. I think you absolutely need to do more tinkering with the system; it’s not set up that well.

I’ll have more thoughts on this topic in due course.