Strawberry Chessmen Banana Pudding
Need a dessert that looks fancy and tastes incredible but secretly takes almost zero effort? This Chessmen banana pudding, jazzed up with sweet strawberries, is the no-bake hero of potlucks and BBQs. It uses iconic buttery Chessmen cookies for a richer flavor, layered with creamy pudding, bananas, and strawberries.
Equipment
- Large bowl
- Whisk
- Measuring Cups
- Measuring spoons
- 9x13 inch Baking Dish or Trifle Bowl
- Knife
- Cutting Board
- Spatula or Large Spoon
- Plastic Wrap
Ingredients
- 2 7.25 oz bags Pepperidge Farm Chessmen Cookies
- 2 3.4 oz boxes Instant Vanilla Pudding Mix (Jell-O brand works great)
- 3 cups Cold Milk whole milk recommended
- 1 14 oz can Sweetened Condensed Milk (Eagle Brand recommended)
- 1 tsp Vanilla Extract
- 1 8 oz container Cool Whip, thawed (or approx. 2 cups homemade whipped cream)
- 4-5 medium Bananas ripe but firm, sliced
- 1 lb Fresh Strawberries about 2 pints, hulled and sliced
Instructions
- Whip up the Pudding: In a large bowl, whisk the instant pudding mix and cold milk for about 2 minutes until it starts thickening.
- Make it Creamy: Whisk in the sweetened condensed milk and vanilla extract until smooth.
- Fold in the Fluff: Gently fold in the thawed Cool Whip or whipped cream until just combined.
- First Layer: Spread a very thin layer of the pudding mixture on the bottom of a 9x13 inch baking dish or trifle bowl.
- Chessmen Layer 1: Arrange a single layer of Chessmen cookies over the pudding, covering the bottom.
- Fruit Layer 1: Top the cookies with a layer of sliced bananas, then a layer of sliced strawberries.
- Pudding Layer 1: Spread about half of the remaining pudding mixture over the fruit.
- Chessmen Layer 2: Add another full layer of Chessmen cookies.
- Fruit Layer 2: Layer the remaining sliced bananas and strawberries over the cookies.
- Final Pudding Layer: Spread the rest of the pudding mixture evenly over the top.
- Chill Time!: Cover tightly with plastic wrap, pressing it gently against the surface. Refrigerate for at least 4-6 hours, but preferably overnight, for flavors to meld and cookies to soften.
Notes
Cookie Substitute: While Chessmen are key, other buttery shortbread cookies (like Walkers) can be used. Nilla wafers result in a more traditional texture. Pudding Options: French Vanilla instant pudding or homemade vanilla pudding can be used.
Fruit Variations: Omit strawberries for a pure Chessmen banana pudding, or swap strawberries for raspberries/peaches.
Dairy-Free: Possible ONLY if using dairy-free pudding, milk, condensed milk, whip, AND a dairy-free/vegan shortbread cookie alternative (Chessmen contain dairy).
Bananas: Use ripe but firm bananas; slice just before layering to minimize browning. Chilling is Crucial: Don't skip the 4-6+ hour chill time! It's essential for the cookies to soften perfectly.
Storage: Store covered in the fridge for up to 3 days. Cookies will soften further over time. Do not freeze
