Preheat oven to 425 degrees.
Using a large, sharp knife, slice the butternut squash in half.
Brush 1 tablespoon of olive oil over the cut portions of the squash and place face down on a lined baking sheet (I use a slip mat to line my baking sheets, but you could also use foil).
Bake squash for 50-60 minutes, or until squash is tender and easy to scoop out of the peel.
While the squash is baking, sauté onion and apple in a small pan with the remaining olive oil over medium heat for 5-6 minutes. Add garlic and sauté for an additional 1-2 minutes, being careful not to let the garlic burn or brown. Set mixture aside.
Remove the squash from the oven and allow to cool for several minutes. Scoop the flesh from the butternut squash.
Add the squash, sautéed mixture spices, and 1 cup of the veggie broth to a blender or food processor.
Puree soup until smooth, adding more veggie broth if it feels too thick. (You can work in batches if everything doesn’t fit into your blender all at once.
Once soup is blended, pour it into a large pot and heat over medium/low heat on the stove until warmed, about 10-12 minutes.
Scoop butternut squash soup into bowls and top with crumbled bacon, sour cream, and a sprinkle of cayenne pepper if desired.