Make the crust: Place both flours, sugar and salt in the bowl of a food processor and pulse a few times to combine. Add the cold butter cubes and pulse just until the largest butter pieces are the size of small peas, 6-8 pulses. Add 4 tablespoons ice-cold water and pulse just until the dough comes together, adding more water by the teaspoonful as needed.
Turn dough out onto a floured work surface (I use parchment paper) and form into a round disk. Roll the dough into a 12-inch round. Transfer dough round to a 9-inch pie dish by gently folding it in half one way and then the other. Unfold dough in pie dish. Trim around edge so that you have an even 1-inch of overhang, fold the edges of the dough under and create a crimped edge as desired. Place pie crust in refrigerator while you prepare the filling.
Preheat oven to 375 degrees F.
Make the chocolate swirl: Place the chopped chocolate in a liquid measuring cup or small bowl. Heat the heavy cream in a small saucepan over low heat just until it comes to a boil, watching it closely. Pour the hot cream over the chocolate and let stand for 30 seconds; stir until smooth. If needed, microwave in 15 second intervals to finish melting chocolate. Set aside.
Make the pumpkin filling: Combine all pumpkin pie filling ingredients in a large bowl. Whisk until smooth.
Stir the chocolate mixture to make sure it’s smooth. To the chocolate, add ¼ cup of the pumpkin filling; stir to combine.
Pour half of the pumpkin filling into the pie crust. Pour about 2/3 of the chocolate mixture over the pumpkin, in a spiral pattern. Carefully pour the rest of the pumpkin on top. Dollop the remaining chocolate over the top of the pumpkin and carefully use a knife to create a swirled pattern, if desired.
Bake pie for 40 minutes, and then cover the crust with foil or pie shields. Continue baking pie for 10-20 minutes more, checking it beginning at 10 minutes and every 5 minutes after that, until center jiggles just slightly when you gently shake pie. Cool pie completely before slicing. Serve with whipped cream, if desired.