This makes for a silky smooth, rich, creamy soup with sophisticated flavor. If you roast the squash ahead of time, this goes together quite quickly. To really do it up, substitute heavy cream for some or all of the milk.
3 lbs winter squash
2 Tbsp butter
2 medium shallots, finely chopped
2-3 cups chicken or vegetable stock
1 bay leaf
1/2 tsp dried tarragon
1 Tbsp white wine vinegar
1 cup whole milk
Salt and pepper to taste
To roast the squash, cut it in half the long way and scoop out the seeds. Preheat the oven to 375 degrees. Place the cut squash face down in a baking pan with edges and pour in about 1/4 inch of water. Roast for 45-60 minutes, until very tender. Allow to cool, then scoop out the flesh.
While the squash cools (or, if you roasted it ahead of time, when you are ready to prepare the soup), melt the butter in a Dutch oven over medium heat. Add the shallots and saute for about five minutes. Add the squash and stock and combine well.
Puree the soup using an immersion blender (or in batches in the blender or food processor) until nice and smooth. Add the bay leaf and tarragon and simmer for 15-20 minutes. Remove the bay leaf and stir in the vinegar, then turn off the heat and stir in the milk. Add salt and pepper to taste.
Serves about 4.