It's understandable, with a wide open outdoors map looking a lot more overwhelming to prepare for, compared to a dungeon map.
For me, there's three parts to the wilderness part of a campaign.
Part 1 - putting down a key. I use Welsh Piper's general approach of that each hex can have a "major" encounter/landmark and several "minor" encounters/landmarks. I do general stocking, without a lot of details. I save those for when the players are going to run into them. I don't do a random encounter table yet.
Part 2 - pre-game prep. Part of the contract I have with my tabletop players is that I need to know a week in advance of their general plans for the game. That allows me to do some in-depth prep. If they're traveling from point a to point b, this is a lot easier, than if they're at a homebase and have several options.
So once I know their general mission, I look at the map and their expected route.
I start with "day 1" of their travel for that game. For my map, the heroes have different travel rates if they're mounted, on foot, on a road or in country.
For each hex that they might travel through, I look at the key. If something is there, I see if they would encounter it. I roll a d6 for major, and a d6 for each minor. If it's a 6, they miss the major. If it's a 1-2, they run into the minor. If they are going to run into something, I'll note which day they run into something.
If it's a major/minor encounter from the map, NOW I will flesh out the details. If it's a dungeon or some sort of place requiring its own map, I'll do a level or two, depending on how strong the party is and if I anticipate they'll be strong enough to go through the whole thing.
I repeat this for the entire trip. So now I have a list of what they will hit/not hit on their journey. And I know how many hexes they run through, and I'll figure out how long this all takes.
THEN, for each day of travel, I roll a (d6 for civilized/populated lands, d8 for less populated, d10 for wild) for day and another for night. If there's a 1, then there's a random encounter with something. I note that on which day as well.
Now I have a "script" of sorts of what the players will run into and when that will happen.
I then flesh out the encounters, whether with a major/minor from the key, or as the result of a random encounter. With random encounters, I know what is logical for that area. I also look to several tables and books for ideas/inspiration. Sometimes previous keys I've made. What am I in the mood for and what have I already done in this area?
I plan out for the entire trip or mission that they've laid out. It might take them a few sessions to do this, but it's easier for me to do it as much as once.
So here's an example:
The players are going to travel from the Town of Golden Gate to the ruined Fort Dawn. They have to travel through the Wild Woods and across orc-held Plains of Woe.
So let's make this easy - it takes 1 day to cross 2 hexes of grasslands, farmlands (mounted). 1 day to cross 1 hex of light woods/hills (mounted). 2 days to cross 1 hex of deep woods.
The "mission" that the players tell me is that they will head east/southeast towards the ruins. They want to avoid the Orcs. They have a ranger with them.
So the most likely path is 00.01 -> 01.01 ->02.01 -> 03.01 ->04.02 ->05.02-> 06.02.
They might run into the "Ancient Stones" in 03.01. That is a major encounter in my key. So I roll a d6 and I come up with ... surprisingly, a 6! So they will miss the major encounter. OK, what about the ruins themselves? That's another major encounter. I roll a 4, they'll find it.
So with that in mind, it will take 6.5 days to go from Golden Gate to Fort Dawn. They will encounter Fort Dawn on day 6.5
So my random checks - day 1, morning is in civilized, evening is in light woods. That's a d6 and d8 to check for encounters. 2 and 6, no encounters. Day 2 is in light woods. 3 and 3, no encounter. Day 3 and 4 are in the deep woods. That's a d10. 7 and 5. No encounter. Day 5 is in light woods, d8 check. 8 and 7, no encounter. Day 6 morning is grasslands, evening is enter the hills. d8 and d10. 1 and 8, aha, finally an encounter! Day 7, morning check only as by afternoon, they'll be at the fort. 4, no encounter.
Jeeze, these guys have it EASY this trip!
Here's the script:
Day 1 - 00.01 (grasslands) to 01.01 (woods) - no encounters
Day 2 - 01.01 (woods) to 02.01 (woods) - no encounters
Day 3 - 02.01 (woods) to 03.01 (heavy woods) - no encounter
Day 4 - 03.01 (heavy woods) - no encounter
Day 5 - 03.01 (heavy woods) to 04.02 (woods) -no encounter
Day 6 - 04.02 (woods) to 05.02 (grasslands) - ENCOUNTER
Day 7 - 05.02 (exit grasslands into hilled grasslands) - no encounter, MAJOR: Fort Dawn
For the grasslands, I roll on a small table and figure out it will be a humanoid encounter. It makes sense that this is a hunting party of mounted orcs. So I come up with the encounter parameters and write it out.
Part 3 - at the table. OK, so we're playing the game.
Me: It's the 8th day of Autumn and you've loaded up your supplies and are ready to leave town. Do you do anything else or do you head out?
Players: We go! Off to the fort!
Me: Well, (reading notes) Fortune smiles upon you, as with the help of the ranger, you have a fairly unventful journey for the first 5 days of your trip. You navigate the Dark Woods without incident, with only the gloom of the heavy canopy marking anything of note during the two days it takes you to get through them. However, on the sixth day, as your horses range through the grasslands... (rattle of dice as I figure out who has surprise)...
Me: Ranger, as you are out ahead of the group a-ways, scouting, you come upon the rear vanguard of what appears to be a group of orcs, riding, unaware that you're behind them! What do you do?
Ranger: I quietly make the "stop/danger" sign, hoping that my friends behind me see it. I then jump off my horse and get it to lie down.
Me: OK - the elves and halfling in the party, roll a d6. If you get a 1 or 2, you see that sign and can warn everyone. Otherwise... this will be interesting!
(The encounter is resolved... so now we continue)
Me: OK, after cleaning from the messy orc encounter, there is still time to travel. Do you wish to continue?
Players: Yes!
Me: OK, the remainder of the day and the following day are uneventful. The tall grasses lead into hill country, mostly covered in the grasses that are tall and fragrant in the autum sun. By midday of the 15th day of Autumn, you see the ruined towers of Fort Dawn on the horizon, sitting on top of the largest of the rolling hills...
And that's really about it.
I used to do a "day by day" blow of moving across the map, and it just wasn't really fun for anyone? I started doing this approach after seeing it suggested online. The players like it, because it focuses on the important stuff.
They do have to track resources, of course and I'll remind them of that when they hit points where they stop.
Questions that I anticipate
What if the players change their mission or go off the script? What if they get lost?
Well, they understand that if they change the plan, I may need to "take a break" in order to figure out what happens when instead of going to Fort Dawn, they decide to stay in the Dark Woods and seek out the Ancient Stones. So at the table, I'll pretty much follow the same approach, figure out the day to day until they reach their new destination.
If that's not appropriate, or they get lost and they're wandering off course, then we drop into a "day by day" mode, which I cover in the next question.
What if they're truly "crawling" around a wilderness to explore?
Then I do the same exact thing, but on a hex by hex, day by day basis. It does slow things down a bit more, because I'm repeating this for each day, but that's pretty much what wilderness exploring is... it's become a different type of game. It's no longer a "travel and destination" game, it's truly seeing what is in each nook and cranny.
Because I've done this enough, I can roll it out pretty fast and get to the jist of things quickly.
What about weather?
Ah, I didn't want to muddy the waters with weather, but yes, weather can be an encounter. I use weather charts that lay out each day's weather - it's the 7 Years of Fantasy Weather almanac that I've podcasted about before. On days where there is weather that seriously affects their travel, that's an appropriate event to call out as a waypoint or encounter. Or I let them know how the weather affects their travel (usually to slow them down).
What other questions did I not think of? What do you think of this approach?
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