Do you have the fair already?
I was asking because you need to finish all of country road's event as well as the bareshade's expansion, to get Logan's second heart and some likes with him, to start the Country road event you need to rescue Vicoria's second prisoner and help him around the farm until he reaches the threshold to take him to visit Bareshade after the visit the event will be on your event log, though you need to have Korg home to progress the event