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In a pot, whisk the vanilla pudding mix and 6 cups of milk until it comes to a boil over medium heat, stirring constantly. Take off the heat and stir in pumpkin puree and pumpkin pie spice. Set aside and cool.
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Repeat process with the chocolate pudding; whisking it into the milk until it comes to a boil.
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In a large bowl, beat cold cream, vanilla extract, and confectioner’s sugar on high with an electric hand mixer for 5 minutes until it forms peaks.
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In a trifle bowl, you can layer the pudding, graham crackers, and whipped cream however you like, but I recommend making sure you have enough whipped cream for the top & using graham crackers in between each layer of whipped cream or pudding.
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For candied pecan topping: in a small saucepan, melt brown sugar with water over low heat, stirring constantly to prevent from burning. Stir in pecans. Cook for one minute, remove from heat, and cool.