Preheat oven to 400 degrees F.
Place the peeled and diced butternut squash and carrots on a baking sheet, drizzle with olive oil, and season with salt and pepper. Bake for 30 minutes. Give the butternut squash a toss with a spatula and cook for an additional 10 minutes.
While the butternut squash cooks for the final 10 minutes, melt some butter in a big soup pot.
Add the onions and cook for 3-4 minutes or until the onions are translucent.
Stir in the garlic, sage, thyme, cinnamon, and apples. Cook for about 2 minutes.
Add the chicken stock, carrots, and roasted butternut squash and let it come to a boil. Season with salt and pepper.
Reduce the heat to low and cook for 20 minutes or until the apples are softened. Remove from heat and discard the sage and thyme.
Blend the soup using an immersion blender. Return the pot to the stove and cook for an additional 10 minutes. Stir in the heavy cream and season with additional salt and pepper if needed.
Garnish with extra cream, fresh sage, or pumpkin seeds.