My favorite Order of the Stick cartoon, back when I enjoyed that strip, concerned the number of random encounters the party should expect while traveling overland to a dungeon.  Here’s the link, but I will summarize: the joke is that despite different travel times, all parties should expect exactly one random encounter when traveling, as “no matter how long the journey, you only have one random encounter before everyone gets bored and moves on to the main plot.”

It struck me as especially funny because it’s exactly what I’ve found myself doing on numerous occasions.  It speaks to the battle between keep the main thing the main thing and the oracular power of dice.  And unfortunately, there’s no real general purpose rule for handling this balance.

I have certainly run plenty of dungeons where the dungeon itself dictates the rate at which one rolls for random encounters.  I have on occasion ignored those roles simply because cool stuff was already happening, and I know that I along with the players would all be irritated if the flow was interrupted by a random monster happening along.  On the other hand, when the party decides to lock themselves in a room and camp for two days, or is simply being slow, loud, and clumsy at moving through the dungeon, those rates of wandering monster rolls are exactly the mechanic I feel justified in applying to balance things out.  Without a tangible downside to slow progress, who wouldn’t spend a full turn carefully searching every 10′ increment of the dungeon for traps, secret doors, etc?

This is exacerbated when traveling in the wilderness.  My preferred campaign setting is a large world littered with small dungeons.  I’ve tried the whole mega-dungeon thing, and while I still find it enticing, for extended campaign play I prefer short and sweet dungeons punctuated by travel to differing towns and some random encounters between, be they monsters or civilized folk.  Still, that means a lot of random rolling when the players start moving around the map, and some times this can really bog down play.  Sometimes the dice just refuse to let up, and after the third or fourth random encounter along the road, it becomes tedious and boring to everyone at the table, the DM included.

On the other hand, our last session was entirely composed of this.  The players were simply trying to travel around the perimeter of a mountain — should be easy, right?  Well there’s no road, and the south side of the mountain borders a place known as “the Gloomwood”, a heavily wooded region rife with lycanthropes and similar such deadly creatures.

So I turned to my random charts.  Here’s the rules from the Expert book I use as my starting point:

When travelling, a party can become lost.  A party following a road, trail, or river, or led by a reliable guide, will not become lost.  Otherwise, the DM checks each day, rolling a six-sided die (1d6) before the party begins movement .

Expert Book, p. X56

While travelling in the wilderness, there is a chance the characters will encounter creatures just as they would in a dungeon.  The DM should decide how often encounter checks are made.  Encounters are usually checked for once per day, but the DM may include planned encounters, or may make additional checks if appropriate.  No more than 3 or 4 encounter checks should be made per day.

Expert Book, p. X57

Charts are then given based on terrain type to show the chances in 6 for each event.  Usually it’s 1 or 2 in 6 for getting lost, likewise for encounters though in some rougher terrains it goes up to 3 in 6.  For well travelled areas I usually skip the lost check and limit the encounter check to once per day.  Sometimes I’ll even increase the die size to further lessen the chance of encounters.  In worst case situations, like say trying to circle around a mountain and avoid the Gloomwood, I will roll 3 checks per day, usually by designating three different colored dice as “morning”, “afternoon”, and “night” and rolling them all together.

So in our last session the party was attempting to circle round the mountain to find an old cave they knew contained a magical scrying pool (similar effect to a crystal ball) which they wished to use to their advantage.  Right off the bat they both got lost and hit an encounter.  I ruled this as them drifting too far south and accidentally entering the Gloomwood, where they were set upon by werewolves.  The next day the same result, lost and one encounter.  This time they overshot the mountain and ended up in the Dead Hills, a place where many ancient battles were once held that is now quite haunted.  The encounter came at night, so the party managed to witness a battle between two forces of undead which they cleverly avoided, though at the cost of losing all the benefits of a good night’s rest (no healing, no spells regained).  On the third day they climbed the mountain where they were set upon by Caecilia (giant gray worms) in a set encounter I had placed there before we even started playing.  They managed to get into the cave, use the scrying pool, and get out in time to make camp just at the tree line below the cave.  Wouldn’t you know it, another random encounter roll released two fire salamanders on them in the middle of the night (did I mention the cave is on the side of a  volcano?)  The party managed to fight them off, and the next day returned to their camp at the base of the mountain, which had been overtaken by an entire tribe of orcs (yup, another random encounter).  Being fairly high level, they managed to kill off the orcs and charm the chieftain, and so ended a full night of adventuring.

And honestly, I think we were all having a great time.  The wandering monster and lost rolls all made sense.  I did re-roll a couple times for the specific monster type when I got stuff that was just crazy, but I never fudged the chances of it happening.  I did not randomize the lost rolls because in both cases the monster type pushed me in a specific direction.  Werewolves?  They must have gone too far south and entered the Gloomwood.  Undead?  Clearly they’ve accidentally entered the Dead Hills.

So, clearly random encounter rolls can actually build some really exciting play.  Unfortunately, sometimes it also leads to tedious play, especially when it’s getting in the way of something exciting that everyone is looking forward to.  Any consistent rule here is simply too rigid to be followed dogmatically.  The DM simply must keep his thumb on the pulse of the table, and adjust the pacing as he sees fit.  While I fight the urge to fudge dice, and actually roll all my combat rolls in front of the screen to avoid the temptation, in the case of wandering monster checks I think it’s imperative that the DM feel a strong latitude to roll or ignore the rolls as he sees fit.

This, I think, is what Gygax was getting at when he described his own DMing style as “free-wheeling.”