One of the things I had the toughest time with back in the day was wilderness exploration, a.k.a. the classic Hex Crawl. Oh, the procedures were straightforward enough: Calculate movement rates through the appropriate terrain, roll for getting lost, roll for encounters, and move the party's position on the map, stopping to play out numbered encounters in any hex they might pass through. The problem, of course, is that this isn't an inherently interesting process, and it becomes mind-numbingly boring after a few repetitions.
My first experience with hex crawls was module X1, The Isle of Dread, that came packaged with the Frank Mentzer-edited Expert Set. The excitement of having new rules for large-scale wilderness exploration (as opposed to the hour or turn-based treks in the Borderlands of B2 fame,) and a plethora of new monsters (Dinosaurs!!) both in the rule book and the appendix of the module pretty effectively offset the tedium of my repetitious methods and the fact that despite its overall coolness, the non-random encounter density of the Isle of Dread was entirely too low.
Eventually, though, the novelty of wilderness adventuring and new monsters became old hat. Most of the time, if the party was headed to a particular destination, I'd just move them along the map toward it without bothering to ask, "Which way do you go?" and roll for encounters en route, while they talked amongst themselves or doodled on their character sheets. Sometimes I'd just roll once for encounters and gloss over the rest of the journey entirely. If there was actual exploration to be done, they would choose a direction pretty much at random, and I'd roll the checks each day, report on their progress in bland generalities ("You're still in the woods." "You enter the mountains.") and ask them which direction they wanted to go the next day. Rarely having been given a reason to change their heading, they'd invariably keep going until they found something either interesting or impassable. If they passed within a hex or two of a fixed encounter location, I'd fudge their direction a little, or else they'd pass it by and never know it.
This probably makes it sound as if I sucked as a DM, and I won't try to wriggle away from that charge. For whatever reason, I just didn't get how it was really meant to be done. Once again, it's a combination of age, hindsight, and the insights of the Old School Renaissance to the rescue. I can see now that one of my biggest failings back then was that I didn't give my players enough information. It's really no wonder they just messed around until I rolled up something for them to fight. They were waiting for something, anything, to inform their decisions. I've seen posts on other sites postulating a system for determining the chances of parties finding something in a given hex, but I don't think that's the answer I've been looking for. Rather, I want an analog solution, an interaction between me and my players, observing and questioning, not merely a die roll. Just like with traps in a dungeon, things should be described, clues should be given openly, and the choice of whether and how to pursue them left to the players.
What would they know about the area without expending much proactive effort, through tavern talk, local folklore, notices posted at the inn, and so on? What else could they find out by digging deeper, asking sages or old timers or eyewitnesses, rooting around in the town archives or library? Trekking aimlessly into the mountains just because the DM says they're there is pretty dull, at least for a game experience. Trekking into the mountains because you've heard that the Crypt of the Mad Dwarf Lord is rumored to be out there somewhere, in a hidden ravine with blue-veined stone, accessible only by rappelling down a steep cliff, makes for an interesting excursion, in which the players know what they hope to find and have some idea of where and how to find it.
What can they see while they're out there in the field? If you have enough points of interest marked on the map, they should be able to learn of the existence of some of them even from a few hexes away. From the top of a hill or the high branches of a tree, explorers should be able to see for miles under decent conditions. Rivers, lakes, a towering spire of rock, a ruined castle on a distant hill, the stone cairns on a gloomy moor, a hamlet with wisps of smoke rising from its hearths, or a twisted and ominous tract of forest could be visible to a party that pauses to survey its surroundings. Even if they're not adventure sites, distinctive landmarks add interest and depth to the setting and provide points of reference. Hey, there's that three-pointed rock! I know where we are now!
What clues are there to be found that might point to the presence of a keyed encounter site without having to pass through its exact hex? If there's an orc lair, there should certainly be well-worn paths that the orcs use for raiding and foraging, perhaps ranging many miles from the lair itself. If there's a ruined castle, there might be ancient remnants of a paved highway or aqueduct, anomalous weathered statues sticking out of stands of bracken, or the foundations of farm houses overgrown with brush. The trees in an owlbear's territory might bear obvious claw marks. Fairy rings of mushrooms might give away the proximity of a stronghold of pixies. Clues can point to a specific direction or course of action, or they can just intrigue the party enough to make them declare that they want to stay in this area and search it more intensively.
How does a random encounter fit into the setting and its current events? If you roll goblins, what are they doing there? Are they on their way to, or just come from a keyed encounter location? Do the friendly elves or dryads have any information that might be of use or interest, and is it specific or vague? Can you add hooks to random encounters? If you roll giant carnivorous flies, they might be feasting on the carcass of a horse with saddle and harness. Whose was it, and what happened to him? Could it have anything to do with a nearby keyed encounter site? Might it lead to something other than what the players are currently pursuing, thus posing a choice to be made?
What terrain clues might inform a party's choice of direction? Does the land slope, and if so, in which direction? Are there brooks and streams that would logically flow toward a major river or lake? Game trails or hunting paths? Do the winds tend to come from a particular direction?
I haven't yet run a real wilderness adventure in my new campaign, but I'm no longer dreading the choice between fun-sapping tedium and glossing over it. I'm actually looking forward to a fun an interesting adventure. Thanks again, OSR.