Whole Roasted Pumpkin Stuffed with Savory Mushroom Bread Pudding

This is an impressive entree, fancy enough to star in your Thanksgiving feast, but simple enough to prepare throughout pumpkin season. We all deserve a few recipes that look far more difficult than they actually are. 

The key to this recipe is the pumpkin itself. Although a cheese pumpkin (a wide, tan variety with beautifully scalloped sides that make them look like Cinderella’s carriage before and after the ball) is ideal, any edible pumpkin with thick, dense, delicious flesh will do. Please don’t try to eat your Jack-O-Lantern pumpkins, which won’t harm you, but will disappoint you because they are meant for decoration, not dinner.

Makes 8 servings.

Preheat the oven to 350°F. Line a rimmed baking sheet with a silicone baking mat, aluminum foil, or parchment paper. (If you have any trepidation about maneuvering the heavy pumpkin in and out of the oven, you can sit the pumpkin inside a large Dutch oven or skillet, although you’ll need to serve it from the pot, which is less dramatic, although just as delicious.) 

To carve out the pumpkin lid, use a short sharp knife (preferably serrated) to cut a circle midway between the stem and the outer edge of the pumpkin, as though starting a jack-o-lantern. Short strokes and a sawing motion work best. It's easiest to work your knife around the top of the pumpkin at a 45-degree angle. Lift out the lid and set it aside. Use your hands or a small sharp spoon to scoop out and remove the seeds and wet fibers. (You can save them to roast separately. Recipe follows.)

Place the pumpkin on the prepared baking sheet. Moisten the outside with oil. Sprinkle the inside with salt and pepper.

Whisk together the half-and-half and eggs in a large bowl. Whisk in the mustard, thyme, sage, 1/2 teaspoon salt, 1/2 teaspoon pepper, nutmeg, and cayenne. Stir in the bread and set aside to soak. 

Warm the butter in a large skillet over medium-high heat. Stir in the leeks and a pinch of salt and cook until tender, about 5 minutes, stirring often. 

Stir in the mushrooms and garlic, and cook until the mushrooms are tender and browned, about 3 minutes, stirring continuously.  

Remove from the heat and let cool for 5 minutes. Stir in 1 cup of the cheese and the parsley.

Spoon half of the bread mixture into the pumpkin, followed by half of the mushroom mixture. Repeat the layers. Drizzle the remaining soaking liquid from the bread over the stuffing, letting it seep down into it. The pumpkin should be full, but not packed hard with stuffing; you might have a bit leftover. Sprinkle the remaining 1/4 cup of cheese over the stuffing.  Replace the pumpkin lid.

Cover with foil and roast for 45 minutes. Remove the foil and continue roasting until a paring knife easily pierce the shell of the pumpkin, about 45 minutes longer. Remove the pumpkin lid during the last 20 minutes so that any standing liquid on top of the stuffing can cook away and the top can brown a bit. (This is a good time to put the pumpkin lid in the oven if you want to use it for garnish. It doesn’t need to cook through since you won’t be eating it, but a short roast will take away the raw look.) If the stuffing remains a bit pale when the pumpkin is done, stick it under the broiler for a couple of minutes.

Remove the pumpkin from the oven and let stand for at least 20 minutes before serving. The pumpkin and filling will stay warm for at least 1 hour. Serve by slicing the pumpkin into wedges, or simply dig in with a giant spoon, making sure to scoop out the tender pumpkin flesh as part of each serving. 

Variations: The stuffing is open to variations. You can add cooked sausage or crisp bacon, for example. You could use onions in place of the leeks. You can replace the bread with cooked rice or other grains.

Make-Ahead: The stuffed pumpkin tends to wrinkle as it cools and does not reheat well, so this dish looks and tastes best served as soon as it’s made. If there are leftovers, however, scoop out the remaining pumpkin flesh, stir it into the remaining filling and reheat together.