Preheat oven to 425 degrees and line a rimmed baking sheet with tin foil or parchment paper. Place the butternut squash on the pan and drizzle each half with olive oil. Rub the oil over the inside of the squash and sprinkle it with salt.
Turn the squash face down and roast until it is tender and cooked through, 40-50 minutes. Set the squash aside until it’s cool enough to handle, about 10 minutes.
Use a large spoon to scoop the butternut squash flesh into your blender. Discard the skin. Add 2 cups stock, being careful not to fill the container past the maximum fill line (work in batches if necessary), and process until smooth.
Add squash puree to a large sauce pot and stir in the remaining broth, cinnamon, nutmeg, cayenne and a pinch of salt and pepper. Cook over medium heat until warmed through, about 10 minutes. Stir in the maple and bourbon, if using, and cream. Continue to cook another 5 minutes. Keep warm over low heat until ready to serve.
Maple Cream:
In a small bowl stir together the sour cream and maple syrup until thoroughly combined. Season with salt and pepper, to taste.
To Serve:
Serve soup hot in bowls with a drizzle of maple cream, chopped pecans and fried sage leaves. Enjoy!