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For cinnamon pastry cream: Whisk yolks and 1/2 cup milk in large bowl.
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Add sugar, flour, vanilla, and cinnamon.
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Whisk until sugar dissolves.
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Bring 1 1/2 cups milk to simmer in heavy medium saucepan over medium heat.
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Gradually whisk milk into yolk mixture.
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Return mixture to same saucepan.
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Cook until custard thickens and boils, stirring constantly, about 2 minutes.
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Transfer to medium bowl.
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Add butter and stir until melted.
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Press plastic wrap directly onto surface.
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Chill until cold, about 2 hours.
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12
(Can be made 2 days ahead.
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Keep chilled.
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14
).
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For pumpkin-caramel sauce: Melt butter in heavy small saucepan over medium heat.
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Add sugar and cook until mixture is deep amber, stirring constantly, about 8 minutes (mixture will be grainy).
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Reduce heat to medium-low.
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Add cream (mixture will bubble).
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Stir until caramel bits dissolve, about 2 minutes.
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Add pumpkin; stir until heated.
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Refrigerate until cold, about 2 hours.
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22
(Can be made 2 days ahead.
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Cover and keep refrigerated.
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24
).
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25
For roasted fruit: Preheat oven to 400F Mix apples, pears, and lemon juice in large bowl.
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Place butter on rimmed baking sheet.
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Heat in oven until butter melts and begins to brown, about 5 minutes.
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Add fruit to baking sheet and toss with butter.
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Roast until fruit is soft and golden, turning with metal spatula every 15 minutes, about 1 hour.
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Cool fruit on sheet.
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31
For assembly: Place ladyfingers, flat side up, on baking sheet.
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Brush with Sherry.
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33
Line bottom of 2- or 3-quart glass trifle dish with single layer of ladyfingers, Sherry side up.
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Line bottom edge with 1 row of ladyfingers, Sherry side in, pressing gently against dish.
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Spoon half of pastry cream into lined dish; smooth top.
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36
Cover with half of fruit.
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37
Drizzle 1/2 cup caramel sauce over.
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Line edge of dish with second row of ladyfingers, Sherry side inches Cover fruit with single layer of ladyfingers.
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39
Spoon remaining pastry cream over.
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40
Cover with remaining fruit.
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41
Drizzle fruit with 1/2 cup caramel sauce.
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42
Line edge of dish with third row of ladyfingers, Sherry side inches Chill at least 6 hours.
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43
(Can be made 1 day ahead.
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Keep chilled.
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45
).
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46
Whip cream, sugar, and vanilla in bowl until mixture holds peaks.
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47
Fill pastry bag fitted with large rosette tip with whipped cream and pipe over trifle (or spoon whipped cream over).
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48
(Can be prepared 3 hours ahead; chill.)
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49
Drizzle whipped cream with 2 tablespoons caramel sauce.
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50
Brush pear slices with lemon juice; arrange decoratively atop whipped cream.
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51
Serve, passing remaining caramel sauce separately.
