Requirements

Hopefully, they addressed the requirements (like "You'll need to bring __" or "You need a knowledgeable guide") before they left. If they didn't, tell them the consequences of not being prepared. If they persist, either bar the way or add some extra challenges to your list.

Once they're in the field, make soft GM moves that threaten the things they need, and/or to show their downsides. Put the guide in danger. Describe how loud the horse and cart are or how heavy the firewood is.

When it's time to make a hard GM move, consider targeting these same resources. What do they do when their guide is injured, or the horse runs off in a panic?

If they no longer have what they need for the journey, make them feel it. Show the downsides or tell them the consequences or just bar the way, and see how they cope.