Preheat oven to 375 F degrees.
Slice the acorn squash in half and scoop out the seeds.
Brush with olive oil (one tablespoon) and sprinkle a tiny pinch of salt over the halves.
Place face up on a baking sheet and bake the squash until the top looks caramelized. (About 30 minutes)
In a pot, pour in the remaining tablespoon of olive oil.
Add the diced onion and garlic and saute until the onion is soft.
Scoop out the acorn squash pulp and add to the pot. Pour in the vegetable broth and seasonings. Cover and bring to a boil.
Allow to boil for 5 minutes, then turn the temperature to low and simmer another 10 minutes.
Use an immersion blender (or regular blender) to liquefy the ingredients.
Add optional parmesan if you don't need this soup to be vegan. Top with homemade croutons.