Preheat the oven to 375 degrees and cut the squash in half, scoop out the seeds, and rub it in olive oil. Place your squash on a sheet pan and roast it for 1 hour.
Once squash is done, place it and all other ingredients in your high-powered Vitamix. Turn your Vitamix blender on and increase the blade speed up to 10 or high. Alternately, you can use the soup setting. Blend for around 4-6 minutes or until it is nice and warm.
Serve in a bowl and enjoy. Garnish with some roasted pumpkin seeds if you are feeling festive.