Here is the full list of all 20 Woolfe - The Red Hood Diaries achievements. It takes around 6-8 hours to unlock all of the achievements on Windows.
Defeat Woolfe on hard.
Chase Woolfe through the woods without dying.
Kill 50 rats.
Unlock 36 diary entries
Escape the guards without dying.
Kill a Tesla guard
Be quicker than the dev's and finish A Forest Adrift in less then 4 minutes and 56 seconds
Kill 20 Fairies.
Finish the harbour on hard.
Drown right after Red tells you she can't swim.
Defeat Woolfe and listen to what Grandma has to say.
Discover all combo's
Visit the outhouse in the Forest Adrift
Defeat the Pied Piper
Kill 100 kickstarter backers.
Unlock 18 diary entries.
Roll...
Defeat the big rat.
Find Reds axe
Unlock 6 diary entries.