This soup is simple and understated but rich, smooth, and elegant with a gorgeous golden color. If you want to punch up the flavor some more, you can double the quantity of roasted garlic. Cook the squash ahead of time by roasting or steaming and, of course, roast the garlic ahead of time too (I usually do a few heads at once and use it over the next few weeks).
1 large shallot, finely chopped
6 cups cooked mashed winter squash
1 head roasted garlic, peeled
4-6 cups chicken stock (or vegetable stock for a vegetarian version)
1-2 Tbsp dry sherry
1/2 - 1 cup cream
Salt and pepper to taste
Heat a little olive oil in a soup pot. Add the shallot and saute over medium head for 2-3 minutes. Add the squash and garlic and mix with the shallots. Add 4 cups of stock and stir well, then puree the soup with an immersion blender (or do it in batches in a regular blender, then return to the pot). Add additional stock if desired, to reach a consistency that you like - bearing in mind that you will still be adding cream. Stir in the sherry and cream until well blended, then add salt and pepper to taste.
For an elegant presentation, add a small swirl of cream to the top of each bowl for serving.