Ask the Alexandrian #26: (Not So) Lost in the Wilderness

E. wrote: My Lost Mine of Phandelver group has decided to go cross-country to find the goblin castle (Castle Cragmaw). They have vague directions from a goblin they spoke to, but I think it’s highly unlikely they could find the base just from the goblin pointing. How should I run this? Or should I just let them find it after a bit of travel? I have some wandering monsters, but I’m concerned that if they go looking and find nothing that it will be frustrating and not-fun. When dealing with this sort of thing, I find it useful to review the possible outcomes. In this case: They find it. They don’t find it and nothing interesting happens while they look. They don’t find it (at least, not yet), but something interesting happens while they’re looking. Getting a good, solid grip on the situation like this makes it a lot easier to clearly understand the choices that you’re going to make. (And, by extension, the choices the players are going to make.) Next, consider — at least in broad terms…