I don't understand the hate that online pundits have for the wandering monster, or that coming from common players, particularly of the later editions. I can only assume it is because the literature did not understand the gift that wandering monsters are, or how to convey the value of this idea to the community. I suppose that has much to do with the flat, lifeless tables that usually accompany every mention of wandering monsters, and the railroad-like nature of most settings. Players are anxious to get to their destinations, like travellers who will drive all night because they resent having to find sanctuary in some city they'd rather bypass than recognize as having its own value.
Speaking for myself, I enjoy stopping when I travel. I enjoy the unexpected discoveries, the opportunities to taste unexpectedly delicious foods being made in some obscure corner of the country ... the delightful views and the languorous pleasantries of some villa or lakeside inn. I don't see journeys as reasons to rush, rush, rush, turning a blind eye to the landscape as though it should all turn black and therefore be less of a distraction between me and my destination. And of all the games where rushing to the end makes the least sense, D&D must be first on the list. The game doesn't end! What in the hell is all the hurry to get to an end, when the "end" is immaterial?
As a DM, every monster stumbled across along the way is an opportunity to set the hook for another adventure, another interesting find, another wild ride. No matter what the monster is, there's always a reason to wonder what it is doing there? What is it's motivation for being? What trajectory across the country is it taking, so that it crosses paths with the party?
We don't have to see the wandering monster as a thing happening in a bubble! If it is a mess of giant insects, are they not part of some infestation? If thieves, perhaps they have some scheme that they're trying to fund by highway robbery ~ a scheme worth considering. If it is some group of pilgrims, perhaps there's a reason to break off and go to the holy site they're visiting; that holy site might imaginably offer things the party never considered. What if it is a wraith, threatening the party while camped one night? What is that wraith's backstory; what horrible series of events ended by the wraith's cursed presence, in this specific spot? These are all stories, aren't they? And I am constantly being told how important it is to get the party to listen to a story and get involved.
Well, have a wandering monster meet them on the road, grab them by the collar and give them a good, hard shake. Even if the players don't decide to stop and investigate, even if they don't think it's their cup of tea, right now ... they won't forget. That wraith isn't going anywhere. If it's an obscure enough roadbed, that infestation might still need cleaning up. The holy site will still be there. And hey ~ whatever happened to those thieves? Did they pull it off?
When the time comes, and the party reaches their destination and gets rid of the big bad, what do you think they'll do? Wait for you to give them another cold adventure? Hell no. One of them will say, "Oh, hey, we're not doing anything right now. Maybe we should check out that holy place and see what's up with that."
There you are. Another adventure, ready made. Before you can say Jack Sprat, the party's invested all over again and you didn't have to do a blessed thing, except to pay a little more attention to a good thing.
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