Thanksgiving Stuffed Roast Pumpkins

Ingredients

• For the roasted pumpkins and squash:
• 4 small sugar pumpkins
• 1 large skin-on kabocha squash, halved and seeded
• Extra-virgin olive oil, for drizzling
• Kosher salt and freshly ground black pepper
• For the mushroom and kale filling:
• 2 tablespoons extra-virgin olive oil
• 1 pound shiitake mushrooms, stemmed, cleaned, and thinly sliced
• 8 ounces lacinato kale, tough stems removed, leaves cut into 1-inch pieces
• 4 tablespoons unsalted butter, cut into 4 pieces
• 2 medium shallots, finely minced
• 1 medium clove garlic, minced
• 2 tablespoons chopped fresh thyme leaves
• 1/4 cup sherry
• 1 tablespoon sherry vinegar
• For the spiced cream:
• 2 cups heavy cream
• 1 cup whole milk
• 1/2 teaspoon ground cinnamon
• 1/2 teaspoon paprika
• 1/4 teaspoon ground nutmeg
• 1/4 teaspoon ground ginger
• Pinch ground cloves
• For the Glaze:
• 2 tablespoons red miso paste
• 2 tablespoons honey
• 1 tablespoon water
• To Finish:
• 10 ounces high-quality rustic bread, cut into 3/4-inch dice and toasted until dry
• 3/4 cup pepitas, toasted
• 3/4 cup pecans, toasted and roughly chopped
• 8 ounces shredded Gruyère cheese

Directions

1. Roast the pumpkins and squash: Set a rack in the middle of the oven and heat it to 350 degrees F (180 degrees C). Cover a rimmed baking sheet with parchment paper. For each pumpkin, use a sharp paring knife to remove the top in a single piece, the way you would for a jack-o'-lantern. Slide the knife around the inside to free the seeds and fibrous pulp, then scoop and scrape the cavity clean with a spoon. Clean the seeds and pulp from the lids with the paring knife as well. Throw the seeds and pulp away, or save them for another use. Do the same with the remaining pumpkins.
2. Arrange the pumpkins, their tops, and the kabocha squash halves, cut side up, on your work surface. Drizzle the cut sides and interiors lightly with olive oil, then use your hands to spread it evenly. Season generously with salt and pepper.
3. Put the tops back on the pumpkins and place the pumpkins on the prepared baking sheet. Add the kabocha squash to the sheet with the cut sides facing down. Roast until the kabocha is soft enough to pierce easily with a paring knife and the sugar pumpkins have begun to soften, 45 minutes to 1 hour. Remove the pumpkin tops so steam can vent, then leave all the roasted squash on the baking sheet to cool.
4. When the kabocha is cool enough to work with, scoop the flesh into a medium bowl with a large spoon. Mash it roughly with the back of the spoon and discard the skin. Season the mashed squash with salt and pepper, then set it aside.
5. Meanwhile, make the mushroom filling: Warm the oil in a large 12-inch stainless steel or cast iron skillet over medium-high heat until it shimmers. Add the mushrooms, season with salt and pepper, and cook, stirring often with a wooden spoon, until their liquid has cooked off and the mushrooms are deeply browned, about 10 minutes. Move the mushrooms to the sides of the skillet, add the kale to the open space in the middle, and cook, stirring frequently, until the kale has softened slightly, wilted, and mingled with the mushrooms, about 3 minutes.
6. Push the mushrooms and kale back to the edges of the skillet and drop the butter into the center. When the butter has melted and started to foam, add the shallots, garlic, and thyme to the middle. Cook, stirring the aromatics the whole time, until they smell fragrant, about 30 seconds. Pour in the sherry and sherry vinegar, stir everything together, season with salt and pepper, and move the mixture to a heatproof medium bowl to cool.
7. Make the spiced cream: Once the squashes have cooled and the kabocha has been mashed, combine the cream, milk, cinnamon, paprika, nutmeg, ginger, and cloves in a large liquid measuring cup and whisk until smooth. Season with salt and pepper to taste.
8. Make the glaze, if using: Whisk the glaze ingredients together in a small bowl and set it aside.
9. Stuff and finish the pumpkins: Divide half of the filling components evenly among the pumpkins, layering them in this order: mashed kabocha squash, bread, mushroom-kale mixture, pepitas, pecans, Gruyère, and spiced cream. Press the filling down gently with your hands, then repeat the same layers with the remaining stuffing ingredients. If you are using the glaze, brush it over the pumpkins and their tops with a pastry brush.
10. Roast the pumpkins on the baking sheet without their tops until the cheese on top has melted and browned lightly, and the pumpkins are tender enough to pierce easily with a paring knife, 30 to 45 minutes. Put the tops back on the pumpkins and roast for 10 minutes more. Take the pumpkins out of the oven and let them cool on the baking sheet for 5 minutes. With a large spatula, carefully move the pumpkins to a serving platter. Serve right away.