Harvest Elegance Trifle with Roasted Apples, Pears, and Pumpkin-Caramel Drizzle

Start with the cinnamon pastry cream: In a large bowl, whisk together the egg yolks and 1/2 cup of whole milk. Add in the sugar, cake flour, vanilla extract, and ground cinnamon, ensuring all ingredients are well combined. In a heavy medium saucepan, bring the remaining 1 1/2 cups of milk to a simmer over medium heat. Gradually whisk the hot milk into the yolk mixture, then return everything to the saucepan. Cook over medium heat, stirring constantly, until the custard thickens and begins to boil, about 2 minutes. Transfer this mixture to a medium bowl, add the unsalted butter, and stir until melted. Cover the surface with plastic wrap and chill in the refrigerator for about 2 hours or until completely cold (this can be prepared up to 2 days in advance).

Next, prepare the pumpkin-caramel sauce: In a small heavy saucepan over medium heat, melt 2 tablespoons of unsalted butter. Once melted, add 1/2 cup of sugar and cook this mixture, stirring constantly, until it turns a deep amber color and becomes grainy, approximately 8 minutes. Lower the heat to medium-low and carefully add the heavy cream; the mixture will bubble up, so stir until the caramel bits dissolve completely. Mix in the pumpkin puree and warm through. Allow the mixture to cool in the refrigerator for an additional 2 hours (this can also be made up to 2 days prior).

For the roasted fruit, preheat your oven to 400°F (200°C). In a large bowl, combine the peeled and cubed Fuji apples, Bosc pears, and fresh lemon juice. Place 2 tablespoons of unsalted butter on a rimmed baking sheet and heat in the oven until melted and beginning to brown, which should take about 5 minutes. Add the apple and pear mixture to the baking sheet, tossing to coat with the melted butter. Roast the fruit for about 1 hour, turning every 15 minutes until they are soft and golden. Allow the roasted fruit to cool.

Now, for the assembly: Arrange the ladyfingers, flat side up, on a baking sheet. Generously brush them with dry sherry. Begin layering in a 2- or 3-quart glass trifle dish by lining the bottom with a single layer of ladyfingers - sherry side up. Add a layer of the prepared pastry cream, smoothing it out evenly. Top this layer with half of the roasted fruit and drizzle with half of the cooled pumpkin-caramel sauce. For added structure, create a second layer of ladyfingers, arranging them sherry side inward against the sides of the dish. Cover with another layer of ladyfingers on top, then add the remaining pastry cream. Finish with the rest of the roasted fruit and another drizzle of pumpkin-caramel sauce. Complete the dish by lining the edge with a third layer of ladyfingers, ensuring they are sherry side in. Cover the trifle and chill in the refrigerator for at least 6 hours or overnight for best results.

For the whipped cream topping, beat together the 2 cups of whipping cream, 2 tablespoons of sugar, and 1 teaspoon of vanilla extract in a mixing bowl until stiff peaks form. If desired, fill a pastry bag fitted with a large rosette tip and pipe the whipped cream artfully over the trifle or use a spoon to dollop it on top. For a finishing touch, drizzle 2 tablespoons of the remaining pumpkin-caramel sauce over the whipped cream. Lastly, brush the 8 slices of Bosc pears with lemon juice and arrange them decoratively on top of the whipped cream. Serve the trifle immediately, passing the remaining pumpkin-caramel sauce on the side.