You'll need a baking dish (such as a large deep Pyrex casserole) large enough to hold the squash (it's important to measure and fit this before you get started), and one that's large enough to create a bain-marie; the squash will sit inside a baking dish that fits inside a larger roasting pan filled with water during baking.
You might have garlicky oil, vegetables and/or risotto left over, depending on the shape of the squash you use and your packing skills; they can be repurposed for another meal.
Make Ahead: The risotto can be made several hours in advance. Vegetables can be roasted a few hours in advance. The squash can be assembled and baked several hours in advance.
Servings: 20 - 24
- 9 cloves garlic, crushed, then finely chopped
- 4 cups olive oil
- 2 to 3 medium (24 ounces) eggplants, cut lengthwise into 1/4- to 1/2-inch slices
- Small handful thyme leaves
- 4 to 6 (16 ounces) zucchini and/or golden squash, cut lengthwise into 1/4-to-1/2-inch slices
- Small handful fresh oregano leaves
- Freshly ground black pepper
- 1 Hubbard squash, 20 to 23 pounds, preferably with a rounded middle
- 3 teaspoons ground white pepper
- 3 teaspoons garlic salt
- 6 to 8 cups cooked (in vegetable or chicken broth) risotto, with about 1 cup freshly grated Parmigiano-Reggiano cheese mixed in
- 1 large sweet onion, cut into thin slices
- 3 or 4 locally grown or vine-ripened tomatoes, cut into 1/2-inch slices
Stir two-thirds of the garlic into the oil, allowing it to sit and infuse the oil.
Preheat the oven to 375 degrees. Line several rimmed baking sheets with parchment paper.
Arrange the eggplant slices in a single layer on the baking sheets. Brush with some of the garlic oil and sprinkle lightly with the thyme. Roast for about 20 minutes or until the slices have softened and just begun to brown. Transfer the roasted slices to a plate as you work; repeat the process to use all the eggplant.
Arrange the zucchini and/or squash slices in a single layer on the baking sheets. Brush with some of the garlic oil and sprinkle lightly with the oregano and black pepper. Roast for 10 to 12 minutes, or until the slices have softened and just begun to brown. Transfer the roasted slices to a plate as you work; repeat the process to use all the zucchini and/or squash. Discard any unused garlic-infused oil or refrigerate and use within a day or two.
Meanwhile, prepare the Hubbard squash: Cut an access hole that's about 5 inches wide at the center top of one of the squash's rounded sides. Use a large metal spoon to extract the seeds and interior matter of the squash, leaving walls that are 3/4-to-1-inch thick. Reserve the cutout piece, because you’ll use it as a lid during baking.
Reduce the oven temperature to 325 degrees; you may need to adjust or remove the oven rack to allow room for the stuffed squash. Boil a kettle of water.
Place the squash in its baking dish, then place the baking dish inside a larger roasting pan. Season the interior of the squash evenly with the white pepper and garlic salt.
Begin the layering by filling the squash with the risotto, making sure to spread it evenly into the corners and edges of the interior. The level of risotto should be slightly less than half the interior depth. Use a spatula to gently press the risotto layer gently, making sure it is compact.
Use the eggplant slices to create the first vegetable layer, making sure to cover the risotto completely. Sprinkle each slice with thyme. The slices can overlap as needed. Use the zucchini and/or squash slices to create the next vegetable layer, sprinkling them with oregano and black pepper as you work. Use the spatula to press these layers.
Use a majority of the onion slices to evenly cover the zucchini layer, then use the tomato slices to evenly cover the onion slices. Sprinkle the remaining third of the garlic over the tomatoes. Cover with the remaining onions. At this point, the squash should be as full as possible. Seal with the reserved lid piece.
Transfer to the oven, leaving the oven door open. Pour enough of the just-boiled water into the larger roasting pan to come halfway up the sides of the squash's baking dish; this will create a hot-water bath. Bake for about 2 3/4 hours; the squash should feel firm.
Use a turkey baster or heatproof cup measure to carefully remove as much hot water as possible from the roasting pan; this will make it easier to transfer the pan to the stove top (off the heat).
Use chopsticks to line the bottom of a wide shallow basket or bowl that's large enough to hold the squash; it's important to keep the squash from direct contact with the bottom surface.
Let stand for 20 minutes before cutting into wedges, which will show the layers, keeping the vegetable lid on to help maintain the integrity of the shape. To keep the squash warm for up to 2 hours, cover it with clean dish towels, tucking them in around the bottom of the squash.
Adapted from Lisa Jorgenson of Washington, who based her recipe on one from Lydia Adelfio of Chevy Chase.
Tested by Lisa Jorgenson and Sarah L. Voisin.
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