Whats the path to finding Chloe in the outskirts? I spent like 1 hour looking around and the "wrong" paths I tried are not even being remembered/marked by the game.
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You don't find Chloe, you find someone to help her.
To be precise, it's the Goblin Witch.
Once you find her, she asks you help her find her hat somewhere south.
Then once you find the hat, if you check it in your inventory it will tell you where to go.
After that her place has a map in the icon.
Finally if you get her to teach you some magic, you'll be able to progress with Chloe by visiting her room during the morning.