Ingredients

1 (2-1/2 lb.) kabocha squash
¹⁄₂ tsp. olive oil
1 ¹⁄₄ tsp. kosher salt
1 ¹⁄₄ cups plus 2 Tbsp. all-purpose flour, plus more for dusting
1 tbsp. granulated sugar
1 stick unsalted butter, frozen
1 cup heavy cream
3 large eggs
¹⁄₂ cup packed light brown sugar
1 tbsp. ground ginger
¹⁄₂ tsp. ground cinnamon
¹⁄₂ tsp. freshly ground black pepper, plus more
¹⁄₄ tsp. chipotle chile powder
1 (2") piece ginger, peeled and finely grated
Whipped cream, for serving

Instructions

Heat the oven to 400°. Halve the squash, and scoop out any seeds and pulp. Rub the flesh with olive oil and ¹⁄₄ teaspoon salt. Pour 3 tablespoons water onto a foil-lined, rimmed baking sheet and arrange the squash halves cut side down. Cover the tray tightly with foil and bake until the squash is soft, about 50 minutes. Transfer to a rack and let the squash cool. Scoop the flesh into a blender and puree until smooth. You should have 3 cups. Reduce the oven temperature to 375°.
In a medium bowl, combine 1 ¹⁄₄ cups flour with ¹⁄₂ teaspoon salt and the granulated sugar. Using a box grater, grate the butter into the flour mixture and, using your fingers, rub the butter into the flour until it forms pea-size crumbles. Pour in 5 tablespoons ice-cold water and continue kneading until a smooth dough forms. Shape the dough into a disk, wrap in plastic wrap, and refrigerate for at least 30 minutes.
On a lightly floured work surface, roll the chilled dough into a 12-inch circle. Transfer the dough to a shallow 9-inch pie pan, trim excess dough from the edge, and crimp the edges. Dock the dough all over with the tines of a fork, cover the dough with a sheet of parchment, and fill with dried beans or pie weights. Set the pie plate on a rimmed baking sheet and bake for 15 minutes. Remove the pie weights and parchment and bake until the pastry is set and lightly browned, about 5 minutes. Transfer to a rack and let cool completely.
In a small saucepan, whisk together the remaining 2 tablespoons flour with ¹⁄₄ cup heavy cream. Bring to a simmer over medium-low heat and cook, stirring, until the mixture begins to bubble and thicken, about 1 minute. Slowly whisk in the remaining ³⁄₄ cup cream and cook, stirring, until the mixture thickens, about 3 minutes. Remove the pan from the heat and let cool.
In a medium bowl, whisk 1 ¹⁄₂ cups of the squash puree with the eggs until smooth; reserve the remaining puree for another use. Add the thickened cream, brown sugar, ground ginger, cinnamon, pepper, chili powder, and grated ginger and whisk until smooth. Pour into the cooled pie crust and sprinkle with a pinch of freshly ground black pepper. Bake the until the filling is just set, about 30 minutes. Transfer the pie to a rack and let cool completely before slicing. Garnish with freshly ground black pepper and serve with whipped cream.

Elizabeth Chin