This luscious, cakelike pudding, made with milk-poached butternut squash batter and crowned with caramel-drenched delicata, rides the line perfectly between side dish and dessert, “kind of like yams with marshmallows,” says Joe Beef’s Red Morin, who serves it with caramel sauce or sweetened whipped cream. For an easy caramel sauce and squash topping (pictured right), double or triple the quantities of delicata and granulated sugar, and repeat step 4 as needed. Or if you want to amp up the savory nature of the dish, nix the caramel and offer grated cheddar at the table.
- 1 lb. butternut squash, cut into 1-inch chunks (about 3 cups)
- 3 cups whole milk
- 1⁄2 stick unsalted butter, softened, plus more for greasing
- 1⁄2 cup granulated sugar
- 1 delicata squash (1 lb.), washed, halved lengthwise and seeded, sliced 1/2 inch thick
- 1⁄2 cup turbinado sugar
- 1⁄2 cup grade B (dark) maple syrup
- 3 large eggs
- 3 tbsp. apple cider
- 2 1⁄4 cups all-purpose flour
- 2 tsp. baking powder
- 3⁄4 tsp. kosher salt
- 1⁄2 tsp. ground ginger
- 1 generous pinch ground nutmeg
- In a medium (4-quart) Dutch oven or other heavy-bottomed pot, add the butternut squash and milk. Bring to a low simmer over medium-high heat, then continue to simmer until the squash is fully tender, about 10 minutes. Set aside.
- Grease the bottom and sides of a large (10-inch) cast-iron skillet or hanging pot with butter. Set aside.
- Drain the butternut squash and discard the milk. Transfer the squash to a medium bowl. Using a metal whisk, mash the squash until mostly smooth. Set aside.
- Fill a measuring cup with 1 1⁄2 cups water and set it next to the stove. In a 12-inch, heavy-bottomed skillet (not the prepared cast-iron skillet), combine the granulated sugar and 1⁄2 cup water. Cook over medium-high heat, stirring occasionally to help the sugar dissolve, until the mixture is simmering and just beginning to brown, about 6 minutes. Immediately stir in 1⁄4 cup water (mixture will bubble vigorously), then carefully add the delicata squash, arranging the pieces so they fit tightly in one layer (omit any pieces that don't fit). Cook the squash in the caramel, adding 1⁄4 cup more water each time the caramel becomes dry, until the squash is softened and lightly browned on one side, 8–10 minutes. Flip the pieces and continue cooking and adding water as needed, until the squash is tender (but not too soft) and well browned, and the caramel is thickened and bubbling slowly, 8–10 minutes more.
- Pour the caramel and delicata squash into the prepared cast-iron pan, arranging the squash in a single layer. Set aside.
- Prepare a fire in a hearth, fire pit, or woodburning oven. Alternatively, set a rack in the center of an indoor oven and preheat to 350°. In the bowl of a mixer fitted with the paddle attachment, beat the butter and turbinado sugar to incorporate. Beat in the maple syrup, scraping down the sides of the bowl with a spatula as needed, then beat in the eggs one by one. Mix in the cider and squash purée.
- In a medium bowl, sift the flour, baking powder, salt, ginger, and nutmeg. Fold the dry ingredients into the squash mixture.
- Pour the batter over the squash in the cast-iron pan, then spread with a spatula to cover (be sure the batter reaches all the way to the edges of the pan).
- Suspend a hanging pot over the fire, rest a skillet on the embers, or bake the pudding in the oven until the batter has risen and a toothpick inserted in the center comes out clean, 42–45 minutes.
- Remove and transfer the pan to a wire rack; let cool 10 minutes. Place a large, flat serving plate atop the skillet and carefully invert. Let cool slightly, then serve.