Preheat oven to 400°F.
Prep your vegetables for roasting. Peel and cube 1 large butternut squash. Cut 1 medium Spanish onion into quarters. Cut 2 small shallots into halves. Finally, cut the top off a head of garlic. Set aside.
In a large, oven-safe pot or dutch oven add squash, onions and shallots. Remove the sage (or rosemary) leaves from their stem and sprinkle over top the vegetables. Cover in 2 tbsp olive oil and 1 tsp salt. Toss to coat.
Coat the open side of your garlic in the remaining 1 tbsp olive oil and sprinkle with a pinch more of salt. Add garlic, open side down, to the pot.
Roast in the oven for 40 minutes, or until the squash is fork tender. Toss halfway to ensure even roasting.
Remove from oven and transfer to the stove top. Squeeze in the roasted garlic and dispose of the peel. Add enough broth to cover vegetables, about 1-2 cups.
Using an immersion blender, blend until smooth. Turn heat to medium-low and mix in 1/2 cup cream and bring to a light simmer. Add apple cider vinegar and taste, adjust with more salt and vinegar until your taste buds are dancing!
