Bean to bar dark chocolate is a revelation. It's got the terroir and backstory of the finest wines, it's a collision of rural farmers and modern technology and markets similar to coffee, and it also brings along the Proustian nostalgia of childhood.
Too many of us have been stuck in a Nestle/Hershey universe for too long. And if your early collisions with dark chocolate aren't positive, it's easy to decide it's not worth the trouble or expense.
[I get at least 10 servings out of a $10 bar, though, so it's hard for it to feel like a ridiculously expensive luxury. If you skip an espresso…]
Here, in no real order, are my favorite brands, all good to start with, all great to stick with. Every one is made by a human, who cares, someone you could meet, engage with and root for.
A few simple understandings and principles:
The percentage matters, in the sense that chocolate that is between 70% and 90% dark is a Platonic ideal of flavor. I avoid flavoring agents like candies, seeds or salt, because what I'm trying to taste is the bean and what the maker has done to bring it to life.
The kind of bean matters. Forastero beans are cheap, easy to grow and not particularly worth seeking out (with a few exceptions). On the other hand, Criollo (particularly the wonderful rare Porcelana hybrid which you can find from Soma and Original Beans) is a party in your mouth–but, alas, the hardest to grow. It's always that way, isn't it? And Trinitario beans are the backbone of this hobby.
The country matters. Yes, with practice, it's actually easy to tell the difference between Madagascar and Colombia.
And finally, the farmer's relationship with the grower matters a lot. Askinosie imports their own beans, and does amazing work with the farmers who work so hard to grow them.
Enjoy. Halloween doesn't have to mean bad chocolate any more! And don't even get me started on candy corn.