Preheat oven to 425 degrees.
Cut, peel and, cube butternut squash as shown on StoneGable
Add cubed butternut squash to a large bowl and add 1 TBS olive oil and salt and pepper.
Turn contents onto a lined parchment baking sheet in a single layer.
Roast for 40 minutes.
Meanwhile, cook the sausage in a dutch oven, breaking it up. When the sausage is cooked through remove to a plate.
Add 1 tsp olive oil to the dutch oven and add the onions. Cook on medium-low heat until the onions are translucent, about 4 minutes.
Add the apple, sausage, and chicken stock to the dutch oven and turn heat to high until it boils. Reduce to simmer. Simmer for 10 minutes.
Turn off the heat.
Add the milk and stir in.
When the butternut squash is roasted add to the dutch oven.
Using an emulsifier blending stick, blender, or food processor blend the soup in batches until smooth.
Dish out and drizzle with a bit of milk, half and half, sour cream, or creme fraise. Serve hot.