• Preheat the oven to 450°F and line a large baking sheet with foil to reduce cleanup later.

Preparing the Vegetables:

• Start with the pumpkin first. Carefully peel the outside of the pumpkin first, then use a sharp knife to split the pumpkin in half. Use a spoon to scoop out the seeds and discard them. Section the pumpkin into smaller pieces, then cube the pumpkin in 1-inch pieces. Place the cubed pumpkin onto the lined baking sheet.
• Next, peel and chop the carrots and onion. Slice the fennel bulb into 1-inch pieces. Peel and cube the apples. Peel the garlic cloves and keep them whole. Add all the cubed veggies to the baking sheet.

Seasoning the Vegetables:

• Drizzle the olive oil and maple syrup over the vegetables, then add the thyme, rosemary, oregano, basil, smoked paprika, ground black pepper, and sea salt. Use your hands to toss the veggies until they’re well coated.
• Pour the wine and ¾ cups of chicken stock into the roasting pan. Cover the pan tightly with foil. This will trap the moisture inside, cooking the vegetables faster.

Roasting Instructions:

• Roast the pumpkin and vegetables at 450°F for 30 to 40 minutes with the foil on, or until the pumpkin is fork tender.
• Remove the foil and continue to roast the vegetables for an additional 30 minutes, until they’re golden and most of the liquids have evaporated.
• Remove the roasted vegetables from the oven and let them cool for about 20 minutes before proceeding to puree.

Making the Soup:

• You can use a blender, food processor, or immersion blender to puree the vegetables.
• If using a blender or food processor, puree the vegetables and pumpkin in batches; I typically puree them in thirds. Because the puree can be quite thick, add 1/3 to ½ cup chicken stock to each batch to help thin out the puree.
• Pour the puree into a large soup pot, then add in the milk and whatever is remaining of the 2 cups chicken stock. Stir the soup, cook over medium heat and bring it up to a simmer. Once the soup has simmered for a few minutes, remove it from the heat and enjoy.

Serving Suggestions:

• Chop the bacon slices into small bits, then add them into a cold frying pan. Cook the bacon over medium heat, until the bacon bits are rendered golden and crispy.
• Remove the bacon bits from the bacon grease and sprinkle the bacon bits over the soup when serving.
• Enjoy this creamy pumpkin soup topped with smoky bacon bits and a splash of cream. If you love cheese, try adding some grated parmesan cheese on top, too. Serve the soup with toasted, buttered bread or grilled cheese sandwich.