Acorn Squash Pie with Anisette Cookie Crust

By Chef Geoffrey Zakarian

Growing up, when all the other kids were out in the cold playing brutal sports like football, I was in the kitchen with my mom rolling pie crust. (Of course, the kids gave me a lot of grief.) This is a sophisticated variation on my mother’s pumpkin pie, one of the first things I learned to make. It's a multipurpose pie, a little bit sweet and a little bit savory, that works equally well for dessert, lunch, or a late-night snack. Sometimes, I treat it like a great big turnover or Pop-Tart and eat it for breakfast alongside a cup of espresso. For dessert, you can serve it with creme fraiche or Whipped Cream (opposite). It's nice cold right out of the fridge (with that hot cup of coffee ) or slightly warmed up (with chilled whipped cream or even ice cream).

Serves 6 To 8 (One 9-inch Pie)

INGREDIENTS

For The Squash

2 medium acorn squash

2 tablespoons canola or other neutral vegetable oil

1 tablespoon kosher salt

For The Cookie Crust

1½ cups finely ground anisette cookies (biscotti), from 10 to 12 cookies

8 tablespoons unsalted butter, melted

For the Filling

1½ cups evaporated milk

½ cup (packed) dark brown sugar

1/₄ cup granulated sugar

1 teaspoon ground cinnamon

½ teaspoon ground ginger

¹/₈ teaspoon ground cloves

¹/₈ teaspoon ground nutmeg

¹/₈ teaspoon ground star anise

Grated zest of 1 orange

4 large eggs, lightly beaten

2 tablespoons dark rum

Pinch of kosher salt

1 vanilla bean, split

Ingredient Note: The anisette cookies (biscotti) can be purchased at an Italian food market or a gourmet specialty food store. Ten to 12 biscotti are enough to provide the 1¹/₂ cups of ground-up cookies called for; biscotti can be flavored with anise, almonds, or hazelnuts.

DIRECTIONS

Prepare The Squash Puree

Preheat the oven to 400°F

Cut the squash in half and scrape out and discard the seeds and stringy parts from their interiors

Drizzle each squash half with the oil

Sprinkle them with the salt

Place them on a baking sheet, and bake until tender, about 1 hour

Remove the squash from the oven and reduce the temperature to 350°F

Allow the squash to cool enough so they are easy to handle

Scoop out the flesh and puree it in a food processor

You should have about 4 cups of puree

Prepare The Cookie Crust 

In a large bowl, mix the cookie crumbs with the melted butter, working the butter into the crumbs with your hands until the mixture holds together. 

Press the crust mixture into a 9-inch pie pan

Cover with plastic wrap and chill for at least 30 minutes.

Prepare The Filling

In a large bowl, combine the squash puree with the evaporated milk, brown sugar, granulated sugar, cinnamon, ginger, cloves, nutmeg, star anise, orange zest, eggs, rum, and salt. 

Scrape the seeds from the vanilla bean into the bowl and mix thoroughly.

Bake The Pie 

Pour the filling into the pie pan 

Place the pie in the oven to bake for about 35 minutes, or until the filling is fully set

When you jiggle the pan, the filling should no longer move; start checking after 25 minutes

Allow the pie to cool for about 20 minutes. 

Cut into wedges and serve warm with a generous dollop of Whipped Cream

Whipped Cream

In a well-chilled medium to large bowl, combine the heavy cream and confectioners' sugar

Scrape the seeds from the vanilla bean into the mixture

Whip vigorously with a whisk until soft peaks form