If you guys want to tie Buttercup to a tree and hide the wagon/supplies so you can move along the trail, you can do so with relative ease; I won't make you roll for that.
I will, however, ask for a marching order along the trail, as well as how close to the trail you are walking should any of you decide to be sneaky by saying something like "I'm following the trail, but staying off of it and instead of being directly on it am off to the side near the trail". I am, of course, talking about the trail headed northwest, but this could apply to the Triboar as well.