I got 50 likes with ste and 1 heart But Nothing about a road.
Finish "Country road" event. I think you get this by having a certain amount of likes with Ste then invite him over to Bearshade. During the event, you have to prepare certain potions and bombs. Wait a few days after finishing the road then visit Ste. You should neither do intimate moments with Ste while Logan (Logan will hate you) is still in the farm nor tell him not to do it while Logan is there (Ste will hate you). Tell Ste instead to do it next time.