My problem is this: I'm used to handling travelling with DM fiat. Think something along the lines of "The travel takes you, eh, what the hell, two days on horse." I play by the seat of my pants, generally, making up cities and kingdoms and merchant guilds and whatnot by the seat of my pants. But I guess it just seems wierd that I've never gotten anywhere trying to run a hex-crawl, wilderness style adventure.
First, determine your rate of travel. If the party is armored, they're hiking 18 mi/day in grassland. Now determine how long it takes to cross a hex. If you have 6 mile hexes, that's three hexes per day; assuming around 8 hours of travel, that's roughly three hours per hex. It's easier if you make up a little cheat sheet like this:
6 miles/hex (two leagues), traveling 9 hours per day, light encumbrance:
trail: 2 hours/hex
clear: 3 hours/hex
hills: 6 hours/hex
mountains: 9 hours/hex
Now you can narrate travel hex by hex, rolling random encounters as you go. Treat each hex as its own unit: it takes X hours to cross, and you pass through such-and-such terrain, and perhaps encounter something interesting. At each hex, the PCs have a choice to change direction, camp, explore the local area, or whatever. For ease of mapping I tend to describe things in terms of hexes, but this is up to you.
I roll encounters based on how dangerous/interesting I want the area to be. In some places I'll just roll once or twice per day, choosing a suitable terrain type, and then pick an appropriate time during the day to stage the encounter. In other places I might roll for every hex traveled. If the party passes near a monster lairl, that's an extra encounter roll, or maybe instead of rolling I'll just make sure they encounter it.
It is easy to fall into a rut of "you pass through two hexes of woods and camp. No encounters. Now you cross a hex of mountains an camp..." Boring. You want to pepper it with interesting details and encounters. Since I find it hard to produce continual variety, I find it's handy to use a cheat sheet of things to include: other travelers, abandoned cottages, homesteds, standing stones, lone trees, beehives, streams, ravines, old campsites, carcass w/vultures circling, etc. Brainstorm and make a good long list, and just pick something suitable from it now and then.
As to the actual handling of travel, for me it would go something like this:
GM: [roll two random encounters (traveler, and a wyvern), and weather (fog)]. You awake and the morning is chill and foggy. The trees are like ghostly giants. Which direction do you want to travel?
PLAYERS: continue west, I guess
GM: make a survival roll to avoid getting lost
PLAYER: rolls (and succeeds)
GM: [checks map, they will cross a hex of grassland] "You travel for a couple of hours across a prairie. The grass is as tall as your waist, and dripping wet from the fog. A bit before mid-day you come to a river. There are low bluffs and the water is deep. You can't see across because of the fog.
PLAYERS: well, we need to cross so lets find a ford
GM: you travel upstream a few miles and find place to make the crossing. [rolls a river encounter: nothing] on the other side the ground rises abruptly in steep forested hills. Continue west? [yes] You break for lunch and then climb the hills, rising above the fog and emerging into sunshine. It is early afternoon. You are startled to see a wyvern flying overhead.
PLAYERS: [scramble for cover, it either doesn't notice or doesn;t care, wait for it to leave]
GM: you continue climibing into the mountains. These are heavily forested with pine, and steep but not especially rocky. After several hours following a river valley the shadows are getting long. You've crossed half a hex. Do you want to push on into the night or find a campsite?
PLAYERS: [update map] Um, we don't want to run into any wyverns in the dark, so lets camp.
GM: you find a sheltered spot between some rocks, sheltered by tall pines. The smell of your campfire fills the area. Someone says "halloo!" and a man comes walking up, with a walking stick and a wide brimmed hat. he has a backpack and a sword.."
That's roughly how I do it.
So I printed out some hexpaper and set myself down to write. But the gigantic white space is kind of off-putting, and I'm not really sure where to start, or what to put in, or what kind of details I should be including.
Put the starting town right smack in the middle, so no matter which way they go there is room to explore. Sketch in some big details in very broad strokes: a range of mountains, some forests or deserts, a river or two, a lake. If you're stuck for ideas, look at some real geography for ideas. (At this point don't fill in hexes, just decide approximately what goes where.) Put in some major destinations (towns, castles, dungeons) some distance away from each other. Think about how big your hexes are and how long it will take to cross them, and leave plenty of space: the getting there is the fun part. If any of these destinations are well-known, maybe add a trail. But be sure to put some things off in the wilderness with no trails!
Now start sketching in hexes around your base town. Most features (forests, hills) will be several hexes wide, at least, but sometimes there will be small areas only one hex big. Fill in the map however you like. now go back over the map and tweak it: add points of interest, little swamps and mysterious standing stones and old ruins and caves and such. You don't need to know what is what just yet, just focus on making a cool map. Try to make some places difficult to reach. A lot of times, once I start looking at the map I get all sorts of ideas what to put on it. Just get teh basic map scrawled out nad that shoudl get you going. And remember, its okay to re-do part or even all if it if you suddenly get a great idea.
now you have a big map, you can pepper it with monster lairs and stuff. Try to think about who preys on whom, who knows about whom, adn their relationship to ny civilization. I like to lcoate some modules here an there on the map for adventyring destinations.
Finally, you can go back and think about your towns nd castles: who lives in this dangeorus wilderness, and why? What do they know about it?
Hope that helps to prime the pump, everyone has their own style.
