The road away from the guild winds through the mountains, becoming rather steep rather quickly. There are other roads that fork off, going North and South to various other mountain cities, but the fastest road to the plains has them traverse steep, rocky roads better suited to goats than ponies.The pony almost stumbles on the edge of a cliff, but Cy manages to grab hold of the reigns and yank pony and cart back onto the path with no goods lost. It’s the gossip of the afternoon... until a slick patch dumps Cy in the mud while the pony stares at him like he’s an idiot.
The next morning is even worse for getting on the road. They've slept on bedrolls, eaten poor food, and it's still the damn crack of dawn. The only advantage is that the ground is starting to level out. They're in the foothills now, a day-wide stretch of forested ground fed by runoff from the mountains before said streams go underground and flow into the reservoir they’re looking for. Compared to yesterday and last night, it’s almost pleasant: a sedate walk through the forest, leading a placid, dumb beast- and also a horse-, marching to certain death.
They stop for lunch in a grove, under the shade of a large oak tree. Trail mix, jerky, and dried fruit makes for a remarkably bland lunch; chewy, crunchy, but ultimately, it all sort of flows together into one bland dried-out meal. The downsides of being on the road.
They resume their journey, hoping for a sign of new terrain by the end of the day. The path here winds through the trees, seeming to want to take the most indirect route possible through the foothills. After a time, they begin to catch glimpses of something moving in the woods ahead, to hear the sounds of hoofbeats on the beaten path. As they draw nearer, they can make out a wagon, drawn by a pair of mismatched horses. The other conveyance seems to be moving erratically, sometimes sticking to the path, sometimes shying away or around something. As they draw closer, they can see why: the horses seem exhausted, drenched in sweat that will likely cool and give them a chill if the driver isn’t careful.
Perception checks, please.