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Maple Pecan Chessmen Banana Pudding with Spiced Pears

This unapologetically rich banana pudding blends Southern charm with cozy fall flavors think maple, pecan, and spiced pears. A crowd-pleaser that layers creamy pudding with bananas, buttery cookies, and nutty crunch in every bite.
Prep Time 20 minutes
Cook Time 10 minutes
Chilling Time 4 hours
Total Time 4 hours 30 minutes
Course Dessert
Cuisine southern
Servings 12 servings
Calories 420 kcal

Equipment

  • 9x13 Baking Dish
  • Mixing Bowls
  • electric mixer
  • Skillet

Ingredients
  

Spiced Pears

  • 2 ripe pears peeled and diced
  • 1 tbsp maple syrup
  • 1 pinch ground cinnamon
  • 1 pinch nutmeg

Pudding Layer

  • 2 boxes instant vanilla pudding mix
  • 3 cups whole milk
  • 1 package cream cheese softened
  • 1 can sweetened condensed milk
  • 1 container whipped topping thawed

Assembly

  • 2 bags Pepperidge Farm Chessmen cookies
  • 4 bananas ripe but firm, sliced
  • 1/2 cup pecans toasted and chopped

Instructions
 

  • In a skillet, simmer diced pears with maple syrup, cinnamon, nutmeg, and a splash of water until soft but holding shape. Cool completely.
  • In one bowl, whisk together milk and pudding mix until thickened. In another, beat cream cheese and sweetened condensed milk until smooth. Fold in whipped topping. Combine both mixtures.
  • Line the bottom of a 9x13 dish with Chessmen cookies. Top with sliced bananas and half of the spiced pears.
  • Spread half the pudding mixture on top. Add another layer of cookies, bananas, pears, and remaining pudding.
  • Top with more cookies and scatter chopped pecans over the top. Cover and refrigerate for at least 4 hours or overnight.

Notes

  • Use lemon juice to prevent bananas from browning.
  • Swap pears or add banana bread cookies for a fun twist.
  • Make it lighter by using low-fat dairy or skipping a cookie layer.
  • Best made a day ahead for peak flavor.
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