Preheat your oven to 400°F (200°C). Cut the acorn squash in half and scoop out the seeds. Brush with 1 tablespoon olive oil and sprinkle with salt and pepper. Place cut-side down on a baking sheet and roast for 30-40 minutes.

Chop the onion, carrots, and celery into small pieces, and mince the garlic. Set aside.

In a Dutch oven, heat 2 tablespoons of olive oil over medium heat. Add onion, carrots, and celery, and sauté for about 5-7 minutes until softened. Stir in the minced garlic and cook for an additional minute.

Scoop the roasted squash into the pot with sautéed vegetables. Pour in the vegetable stock, sage, thyme, and rosemary. Stir everything together.

Bring to a boil over medium-high heat, then reduce to low and let simmer uncovered for about 25 minutes.

Blend until smooth using an immersion blender or countertop blender.

Return the blended soup to low heat. Stir in half and half cream, adjusting for creaminess. Season with salt and pepper as needed.

Ladle the soup into bowls, topping creatively with honey, red pepper powder, or cinnamon if desired.