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you can check the event log for country road 

is there a certain event that needs to be completed or a quest?

you need to visit  bareshade with him, then sleep until morning - beware, i think that nightmare sleep until mroning keep interrupting how q work and it is bugged, so i just sleep until morning and reload until nightmare doesnt trigger, and it triggers Ste event instead

you can do nightmares during the event. you won't lose any of the 5 days. The nightmares just make it confusing...

Just to recap (and sorry if I am acting dumb) I need to sleep till morning then go to bareshade and not forest path to meet him?

Are you checking your Quest Log? It should tell you what step you are on and any prerequisites that still need to be met.

It doesnt show up, the only active quests i have (mainly cause its still a WIP) the northcrest, rat problem and full moon. Unless i nee to clear one of those then i am locked from the quest.

I am having the same problem the thing is that I cant sleep till morning cause Korg always wakes me up at 2am when he kicks a bandits ass