The game is terrible at communicating this, but the first shadow you encounter - the one in the first ice room with a narrow path - drops a sword when defeated. And it's the only shadow that fight back.
Apparently there are two types of enemies:
- Random encounters - those Weak Shadows
- Bosses - I encountered 4 so far (that first Shadow, Vampire, Sorcerer, Minotaur). The Vampire drops a shield, and you can buy a hat from a shopkeeper for 200 gold, IIRC (I used a task automation tool to grind weak shadows lol).
Those 3 paths? the left one leads to the shopkeep and a rest place, the right lead
Not that I expect you to come back to the game. It's objectively terrible. "Okay" is a compliment to a game like this. It only gets kinda okay later on, which is unacceptable.
I mean, I've gotten far enough, I'll finish it. But you don't have to.