Yes, he has been to bareshade, & I talked to both logan and bernard about setting up the road. The game is currently acting like the road was built whenever he comes to the fair (woman suggested kids playing) but the road has never been built.
If i had to take a wild guess, maybe the game is built so you're not supposed to be able to invite him to bareshade until the town has been upgraded. Pretty sure i still hadn't romanced bernard when ste first came to town. So maybe the game wasnt sure what to do about that and never triggered it.