Heat the oven: Preheat to 425°F (220°C). Line a baking sheet with parchment for easy cleanup.
Prep the squash: Halve the acorn squash lengthwise and scoop out seeds.
Cut each half into 2–3 wedges for quicker roasting. Leave the skin on; it will blend smoothly later or peel easily after roasting.
Season and roast: Place squash on the sheet. Drizzle with 2 tablespoons olive oil and 2 tablespoons honey.
Sprinkle with 1 teaspoon salt and a few grinds of pepper. Roast cut-side down for 30–40 minutes, until fork-tender and caramelized at the edges.
Sauté aromatics: While the squash roasts, warm 1 tablespoon olive oil and the butter in a large pot over medium heat. Add chopped onion and a pinch of salt.
Cook 6–8 minutes until soft and lightly golden. Stir in minced garlic for 30 seconds until fragrant.
Add warm spices: Stir in cinnamon and nutmeg for 10 seconds to bloom their flavor. If using thyme or sage, add now.
Scoop the squash: Let the roasted squash cool just enough to handle.
Scoop flesh from the skin and add to the pot. If some skin slips in, it’s fine—acorn squash skin gets tender.
Add broth and simmer: Pour in 4 cups broth. Bring to a gentle simmer for 8–10 minutes to let flavors mingle.
Blend until silky: Use an immersion blender to puree until smooth.
For a ultra-velvety finish, transfer to a countertop blender in batches. If too thick, add more broth to reach your preferred consistency.
Finish with cream and honey: Stir in 1/2 cup cream or coconut milk. Taste and adjust: add another drizzle of honey if you want more sweetness, salt and pepper for balance, and a teaspoon of lemon juice or cider vinegar to brighten.
Serve: Ladle into bowls.
Garnish with a swirl of crème fraîche or yogurt, cracked pepper, and toasted pepitas for crunch.