With not many good market days left, Dread wasn't going to waste time. Even if things were still strange, he had work to do. Trading for supplies, doing the boring day-to-day shit. Especially in the wake of the last raid, he's in good shape to make the trip without strain. That, and he had the best relationship with the dealers, even if he wasn't about to take advantage of anyone's kindness.
End season goods, what could he pack to offer them? Rations, portioned for the road, packed tidily. A few bottles of late summer brew, some warm layers to add to bedrolls, the scrap hinges that he was still trying to offload, and a pile of ornamental somethings that Kenway or Wake had stashed in the makeshift cart. Wake had been terribly proud of the contraption, and he wasn't about to let the kid down without at least trying. Is this what it is to be an older sibling?
Fast trip, up and back. Even on a fast trip, he wasn't going to be stupid about it. Slowing in the heat of the sun, he can see the woman not far off. "Long walk?" It's a loose, careful greeting. Dread would give her space, not wanting to apply undue pressure. Letting her know she isn't alone, but hopefully that he's not a threat, either.