Preheat the oven to 350 degrees and lightly oil a large roasting pan or casserole. Place squash, carrots, celery, onions, whole peeled garlic cloves, sage, thyme, salt, & pepper in a large mixing bowl. Drizzle with remaining 4 Tbs Olive Oil and toss to coat.
Transfer vegetable mixture to prepared roasting pan and roast for 1 hour; if some vegetables aren't yet tender, remove the ones that are and continue to roast and check back every 10-15 minutes or so.
Transfer roasted vegetables to a large stock pot, removing stems from the herbs as you go. Add about half the vegetable broth to the mixture and puree with an immersion blender. Add cinnamon and continue adding broth a bit at a time, pureeing until mixture is smooth between each addition. Taste for seasoning and serve.
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