How to roast pumpkin:
Using fresh pumpkin really adds to this recipe. Cut a fresh pumpkin in half, scoop out the seeds and guts, and then roast (cut side down) on an oiled sheet pan at about 425°F for about an hour. Let cool enough to handle, then scoop out the flesh and puree in a food processor. Spread the puree out in a sheet pan and bake at 350°F; it is done when it darkens slightly or shows cracks. The second roast is optional but, in my opinion, critical. It reduces the water content of the pumpkin while concentrating the flavor. Cool completely before using in recipe. I recommend doing this in large batches and freezing so it is ready when you need it.
Pour the rum into a small heatproof metal bowl. Sprinkle the gelatin over the rum and let it stand for about 10 minutes, or until soft.
In a large mixing bowl, combine the pumpkin, sugars, egg yolks, orange zest, cinnamon, vanilla, nutmeg and salt. Whisk until combined.
In a 2-quart saucepan, add water to a 1-inch depth. Heat the water to boiling, then reduce to simmer. Set the bowl of softened gelatin over the simmering water. Heat and stir until the gelatin is dissolved. Immediately whisk the hot mixture into the pumpkin, making sure it is well-blended.
In a large mixing bowl, beat 1 1/2 cups cream on high until soft peaks form. Gently fold the whipped cream into the pumpkin mixture and set aside. Do not over-beat.
In a large mixing bowl, beat 1 cup cold heavy cream until it begins to thicken. Add 1 Tbsp. granulated sugar and 1 tsp. vanilla and beat on high until soft peaks form. Do not over-beat as you want it to be creamy, not stiff.
This can be assembled as a trifle or in individual parfait glasses. Divide half the pumpkin mixture into 12 small parfait glasses, or one trifle bowl. Divide half the chopped cookies on top of the pumpkin mixture, then top with half the sweetened whipped cream. Repeat layers and garnish with half of a whole cookie, if desired. Cover and refrigerate until ready to serve. — Michael Sclafani