Chestnut soup, chestnut dressing, chestnut desserts—all remind us of the British roots of many traditional Yankee favorites. Make this hearty soup part of your everyday repertoire by using preroasted, vacuum-packed chestnuts.
Note: Using preroasted, vacuum-packed chestnuts sold in glass jars makes this soup incredibly easy. Look for them in supermarkets during the holidays and in most gourmet and Whole Foods stores year-round (a warning, though: they can be expensive off-season). Don’t use the canned type, which generally lack flavor. To roast chestnuts yourself, cut an X through the flat bottom of each nut (this helps with peeling later). Toss chestnuts with salt, pepper, and ⅓ cup canola oil. Spread on a baking sheet and roast at 425° until tender, 25 to 35 minutes. Return chestnuts to the bowl, toss, and cover bowl with plastic wrap. Cool, then peel.
In a 4- to 5-quart heavy-bottomed pot over medium heat, cook bacon until very crispy. Drain bacon on paper towels, then crumble and set aside.
Drain off all but 3 tablespoons bacon drippings from the pot, then add olive oil, onion, celery, and carrots, and cook, stirring often, until onion is golden brown, 12 to 15 minutes. Add apple, bay leaves, and salt, and cook for 3 minutes, then add broth, scraping the bottom of the pot with a wooden spoon to pick up browned bits. Add chestnuts and cook until very tender, about 15 minutes.
Remove the bay leaves, then purée soup using an immersion blender or process in batches in a regular blender. Return the puréed soup to the pot. Stir in the cream and taste for salt; add more of either, if desired. Serve warm, sprinkled with reserved bacon.