For the Crust
- 13 whole graham crackers, (to yield scant 2 cups crumbs; 6 3/8 ounces), broken into pieces
- 1/4 cup sugar
- 1/4 teaspoon salt
- 6 tablespoons unsalted butter, melted
- 4 ounces bittersweet chocolate, or semisweet, melted
For the Filling
- 1 pound cubed, peeled butternut squash
- 1 tablespoon unsalted butter, melted
- 6 tablespoons whole milk
- 2 large eggs
- 2/3 cup pure maple syrup
- 1/2 teaspoon salt
- 1 teaspoon vanilla extract
- 1 teaspoon ground cinnamon
- 1/2 teaspoon ground ginger
- 1/8 teaspoon ground cloves
- 1/4 teaspoon freshly grated nutmeg
For the Glaze
- 1 cup pomegranate juice
- 1 tablespoon cornstarch
- 1 cup fresh or frozen cranberries
- 1/4 cup sugar
- 2/3 cup pomegranate seeds
Preheat the oven to 375°F.
To make the crust: In the bowl of a food processor, pulse the graham crackers, sugar, and salt until fine crumbs form. Add the melted butter and pulse to combine. The mixture should feel like wet sand. Spread out in a 10-inch tart pan with a removable bottom and press the crust in, taking care to build up the sides so you’ll have a nice top edge. Bake for 8 to 10 minutes, until the crust is golden. Set aside to cool for 10 minutes, then spread evenly with the melted chocolate. Set aside to cool completely while you make the filling. Briefly freeze to harden the chocolate if it hasn’t firmed up by the time you’re ready to fill it.
To make the filling: Toss the butternut squash with the melted butter, spread out on a baking sheet, and roast until tender and golden, turning occasionally, 35 to 40 minutes. The tip of a paring knife should slide in easily when the squash is done. Let cool slightly.
Reduce the oven temperature to 350°F and line a baking sheet with parchment paper.
Transfer the squash to a blender and add the milk, eggs, maple syrup, salt, vanilla, cinnamon, ginger, cloves, and nutmeg. Blend until smooth. Pour into the cooled crust, place on the prepared baking sheet, and bake until slightly puffed at the edges and the surface looks dry and set in the center, 35 to 40 minutes. Transfer to a cooling rack; when it is cool enough to handle, gently loosen the tart from the ring to make sure it doesn’t stick. Leave the ring on and cool completely. Once cooled, put a few toothpicks in the tart to keep the plastic wrap off of the surface and wrap securely in plastic wrap. If not serving right away, you can refrigerate for up to 2 days. I prefer to glaze the tart a few hours before serving no matter what. Once you glaze it, it’s better if you don’t have to wrap it again.
To make the glaze: In a small bowl, slowly whisk the pomegranate juice into the cornstarch until smooth. Place in a small saucepan and add the cranberries and sugar. Bring to a boil over medium heat and cook, stirring occasionally, for 5 to 10 minutes, until the cranberries have all burst and are very soft. Let cool slightly, then pass through a sieve set over a bowl, using a rubber spatula to squeeze out all of the liquid. Scrape the back side of the strainer to get any excess and stir the glaze. If it looks too thick to pour smoothly, add a few drops of water. Pour the glaze over the tart (it can be chilled or just cool enough to handle) and tip it around so the glaze is even. Decorate the edge with a wide band of pomegranate seeds. Chill until ready to serve.
Up to 2 days ahead: Bake the tart shell, line with chocolate, and wrap tightly when cooled. Make the filling and glaze and refrigerate.
Up to 1 day ahead: Fill the tart with squash mixture, bake, and cool. Seed the pomegranate.
Up to 3 hours ahead: Glaze the tart and garnish with the pomegranate seeds.