Autumn Trifle with Roasted Apples, Pears, and Pumpkin-Caramel Sauce

PreparationFor cinnamon pastry cream: Whisk yolks and 1/2 cup milk in large bowl. Add sugar, flour, vanilla, and cinnamon. Whisk until sugar dissolves. Bring 1 1/2 cups milk to simmer in heavy medium saucepan over medium heat. Gradually whisk milk into yolk mixture. Return mixture to same saucepan. Cook until custard thickens and boils, stirring constantly, about 2 minutes. Transfer to medium bowl. Add butter and stir until melted. Press plastic wrap directly onto surface. Chill until cold, about 2 hours. (Can be made 2 days ahead. Keep chilled.) For pumpkin-caramel sauce: Melt butter in heavy small saucepan over medium heat. Add sugar and cook until mixture is deep amber, stirring constantly, about 8 minutes (mixture will be grainy). Reduce heat to medium-low. Add cream (mixture will bubble). Stir until caramel bits dissolve, about 2 minutes. Add pumpkin; stir until heated. Refrigerate until cold, about 2 hours. (Can be made 2 days ahead. Cover and keep refrigerated.) For roasted fruit: Preheat oven to 400°F. Mix apples, pears, and lemon juice in large bowl. Place butter on rimmed baking sheet. Heat in oven until butter melts and begins to brown, about 5 minutes. Add fruit to baking sheet and toss with butter. Roast until fruit is soft and golden, turning with metal spatula every 15 minutes, about 1 hour. Cool fruit on sheet. For assembly: Place ladyfingers, flat side up, on baking sheet. Brush with Sherry. Line bottom of 2- or 3-quart glass trifle dish with single layer of ladyfingers, Sherry side up. Line bottom edge with 1 row of ladyfingers, Sherry side in, pressing gently against dish. Spoon half of pastry cream into lined dish; smooth top. Cover with half of fruit. Drizzle 1/2 cup caramel sauce over. Line edge of dish with second row of ladyfingers, Sherry side in. Cover fruit with single layer of ladyfingers. Spoon remaining pastry cream over. Cover with remaining fruit. Drizzle fruit with 1/2 cup caramel sauce. Line edge of dish with third row of ladyfingers, Sherry side in. Chill at least 6 hours. (Can be made 1 day ahead. Keep chilled.) Whip cream, sugar, and vanilla in bowl until mixture holds peaks. Fill pastry bag fitted with large rosette tip with whipped cream and pipe over trifle (or spoon whipped cream over). (Can be prepared 3 hours ahead; chill.) Drizzle whipped cream with 2 tablespoons caramel sauce. Brush pear slices with lemon juice; arrange decoratively atop whipped cream. Serve, passing remaining caramel sauce separately.

PreparationFor cinnamon pastry cream: Whisk yolks and 1/2 cup milk in large bowl. Add sugar, flour, vanilla, and cinnamon. Whisk until sugar dissolves. Bring 1 1/2 cups milk to simmer in heavy medium saucepan over medium heat. Gradually whisk milk into yolk mixture. Return mixture to same saucepan. Cook until custard thickens and boils, stirring constantly, about 2 minutes. Transfer to medium bowl. Add butter and stir until melted. Press plastic wrap directly onto surface. Chill until cold, about 2 hours. (Can be made 2 days ahead. Keep chilled.) For pumpkin-caramel sauce: Melt butter in heavy small saucepan over medium heat. Add sugar and cook until mixture is deep amber, stirring constantly, about 8 minutes (mixture will be grainy). Reduce heat to medium-low. Add cream (mixture will bubble). Stir until caramel bits dissolve, about 2 minutes. Add pumpkin; stir until heated. Refrigerate until cold, about 2 hours. (Can be made 2 days ahead. Cover and keep refrigerated.) For roasted fruit: Preheat oven to 400°F. Mix apples, pears, and lemon juice in large bowl. Place butter on rimmed baking sheet. Heat in oven until butter melts and begins to brown, about 5 minutes. Add fruit to baking sheet and toss with butter. Roast until fruit is soft and golden, turning with metal spatula every 15 minutes, about 1 hour. Cool fruit on sheet. For assembly: Place ladyfingers, flat side up, on baking sheet. Brush with Sherry. Line bottom of 2- or 3-quart glass trifle dish with single layer of ladyfingers, Sherry side up. Line bottom edge with 1 row of ladyfingers, Sherry side in, pressing gently against dish. Spoon half of pastry cream into lined dish; smooth top. Cover with half of fruit. Drizzle 1/2 cup caramel sauce over. Line edge of dish with second row of ladyfingers, Sherry side in. Cover fruit with single layer of ladyfingers. Spoon remaining pastry cream over. Cover with remaining fruit. Drizzle fruit with 1/2 cup caramel sauce. Line edge of dish with third row of ladyfingers, Sherry side in. Chill at least 6 hours. (Can be made 1 day ahead. Keep chilled.) Whip cream, sugar, and vanilla in bowl until mixture holds peaks. Fill pastry bag fitted with large rosette tip with whipped cream and pipe over trifle (or spoon whipped cream over). (Can be prepared 3 hours ahead; chill.) Drizzle whipped cream with 2 tablespoons caramel sauce. Brush pear slices with lemon juice; arrange decoratively atop whipped cream. Serve, passing remaining caramel sauce separately.