In disguise.

You tell your friends “We have one main problem going there. Between us and there is a fast flowing river, and the only way across is bridge with a town at one end of it. This makes it perfect for catching people trying to cross the river. The only other path is to go deep into the mountains and try finding a way across there, while being hunted.”

Jane frowns. “How are we going to get pass there?”

You smile. “By pretending to be adventurers, or at least one. I am almost ready to multiclass into Rogue when I next level up. If I can do that, I could just tell the guards that I’m bringing some whores to some friends waiting outside of the town. They will be expecting a Scavenger, and not a Rogue.”

Thinking a bit you add, “If you can kill some people away from the contract and level up, it would allow you to multiclass out from being Whores, but we’d need to check you details.”