Preheat the oven to 400 F.

Peel and remove the seeds from the butternut, acorn squash, and pumpkin. Chop into cubes and place in a deep baking dish. Quarter the sweet onion and peel and chop the apple. Add those to the baking dish as well and season with salt, pepper, red pepper flakes, nutmeg, and thyme. Drizzle the olive oil overtop and mix it thoroughly. Slice the top off the head of garlic, drizzle olive oil overtop, and turn it face down in the pan. Bake for 35-40 minutes, stirring about every 10 minutes.

In your soup pot or Dutch oven, add the butter. Let it brown and then add the chopped sage. When the squash is done cooking, add it to the pot. Squeeze the roasted garlic out into the pot. If you are using canned pumpkin, add it at this step. Stir and then add in the broth. Cover and let it come to a simmer.

Once simmering, use an immersion blender to blend the soup completely. You can also transfer to a regular blender and blend the whole thing in that.

Add in the tortellini into the soup and cook for about 5 minutes (this will depend on the type of tortellini you have, usually the precooked ones say they cook in around 2-3 minutes in boiling water).

Stir in the half and half and parmesan and serve. Top with fresh chopped sage, black pepper, red pepper flakes, parmesan, and maybe even some toasted bread on the side!