Preheat oven to 375 degrees F. On two large half sheet pans, add all squash, sprouts, shallots, garlic, thyme. Put the bread on the end of one sheet pan. Drizzle olive oil and sprinkle salt over ingredients and lightly toss with hands, keeping bread separate.
Bake for 7-8 minutes, until bread is golden brown and remove that, setting aside. Return pans to oven and continue to roast for 30 minutes, until all vegetables are tender. Remove from oven and pick out the roasted garlic.
Blend garlic plus all vinaigrette ingredients in a small blender of food processor. Combine all vegetables on one pan and add toasted bread and tart cherries.
Pour vinaigrette over stuffing and stir. Serve warm.