Preheat your oven to 400°F and line a baking sheet with parchment paper. Cut your pumpkin in half, scoop out seeds and stringy bits, then brush the flesh with 2 tbsp olive oil. Place cut-side down on the prepared baking sheet and roast for 35-40 minutes until flesh is completely tender and slightly caramelized at the edges.
While pumpkin roasts, heat remaining 1 tbsp olive oil and butter in a large Dutch oven or pot over medium heat. Add diced onion and sauté for 5-7 minutes until softened and translucent, then add minced garlic and cook for 1 minute until fragrant.
Once pumpkin is done roasting, scoop the soft flesh from the skin and add it directly to the pot with sautéed onions. Pour in vegetable broth and bring everything to a gentle simmer for 5-10 minutes to marry the flavors together.
Add ground sage, ground thyme, and nutmeg to the pot, stirring well to distribute spices evenly. This roasted pumpkin soup recipe develops deeper flavor when spices bloom in the warm broth for 2-3 minutes before blending.
Using an immersion blender, puree the soup until completely smooth, or carefully transfer batches to a regular blender and return to pot. Stir in heavy cream and adjust seasoning with salt and pepper to your preference.
Meanwhile, heat a small skillet over medium heat and toast pumpkin seeds with honey for 3-4 minutes until lightly golden and fragrant. Reserve these for garnish.
Ladle the creamy fall soup into bowls and top with toasted pumpkin seeds, a drizzle of olive oil, and fresh cracked pepper for elegant presentation.