I mentioned about organizing a Curse of Strahd campaign through expeditions more than once. Here's how I'd do that.
(This has nothing to do with the book "Expedition to Castle Ravenloft", by the way...)
First, fix the distances. They are too small, for several reasons. The valley feels crowded, there is a settlement every couple of hours in the road (if you count encampments, ruins, etc.). The distances also allow you to move freely between villages without ever risking spending the night outside. I'd prefer something a bit scarier...
(BTW, make sure the PCs know that sleeping outside in Barovia is dangerous. Villagers are afraid to go out at night, etc.)
The method of checking for encounters is inefficient; you check every 30 minutes, UNLESS you already had 2 in the last 12 hours. So, in theory you would roll 24 times (a complete waste of time) but in practice you will always get 2 encounters every 12 hours, no matter if day or night, IF you ever spend 12 hours outside (because probabilities). What's worse, if you DO have a couple of encounters in the afternoon, you wouldn't check for encounters when sleeping outside?
So you could just roll a couple of d12s to find the time of the next encounter... But the game makes you count hexes, convert distances to time, and then check for encounters.
What about doing this, instead?
- Make the distance between the village of Barovia and Vallaki about 8 hours though the encampment, 10 hours if you avoid it. So, if you make a short rest, you must perform a forced march and risk exhaustion... or make camp and spend the night outside.
- To make things easy, travels between Vallaki, Krezk, Berez, Argynvostholt, Van Richten's Tower and Wizard of Wines take about 6 hours, with two exceptions: it takes 8 hours from Vallaki to WoW, and also 8 hours from Berez to Argynvostholt. Six hours? This means we don't have to sleep outside, right? Well, yes... but consider the way back!
- It takes 2 hours to get from WoW to Yester hill, or from Krezk to Werewolves' Den (through the woods).
- The road to the Ambler Temple should be an expedition unto itself; let's make it sixteen hours. Divide this as you see fit; the last few hours should be a hard hike on the cold mountains...
Now, how we deal with encounters? Roll 1d6 every couple of hours. Add +1 if you stray off the road, +1 if you're travelling at night, +2 if both. You get an encounter if the result is 4 or more (amke that "natural 6" especailly nasty if you want to).
In some cases, especially during the day, you can avoid this encounter with a successful Survival (etc.) check, if you want to. And some monsters might avoid you... but not always (see below).
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Day, night, and the moon-induced bloodlust
The second step in our journey is making travelling during the night very scary. This accomplishes a few things.
It forces characters to look for shelter when they sleep outside. Places such as the Old Bonegrinder, the Tser Pool Encampment, and the tower near Tsolenka Pass are ideal for that. In addition, makes villages and their inhabitants (and leaders, etc.) a lot more relevant - if you make lots of enemies, you cannot find a safe place to rest...
It also makes them consider transportation more seriously - now they need some Vistani as allies, intead of considering the whole people their enemies.
Nighttime encounters are already harder than the ones you have during the day... but I'd spice things up even more. Maybe let the first round of attacks against the PCs have advantage (or double damage, crit on a 19-20, etc.) during the night, as the evil creatures of Barovia are taken by some kind of bloodlust... most will attack immediately and fight to the death. Werewolves get a couple of rounds like that in the full moon, and so on.
Playing around with the phases of the Moon is another advantage of having greater distances, since characters will take at least a few weeks before defeating Strahd. But this is the subject for another post.
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