Stumpy isn't really wandering; she is lost! Oh, I hope they find her!!
Don't they always say to stay in one place if you are lost? That way when someone is looking for you it makes you easier to find!
I think he means that it's pointless to look for Stumpy because she's lost and wandering aimlessly.
I think if Kona tries to find Stumpy he will not because there are usually lots of turns on roads, and Stumpy is also farther ahead than Kona. But I think the owl means wanderers go place just randomly and Kona will have to wait until Stumpy finds him.