Need a dessert that looks fancy and tastes incredible but secretly takes almost zero effort? Honey, let me introduce you to this Chessmen banana pudding, jazzed up with sweet strawberries. It’s the no-bake hero of potlucks, BBQs, and basically any Tuesday night when you need a serious pick-me-up. Forget turning on the oven; this is pure layered magic using those iconic buttery cookies. It’s a delightful upgrade to the classic strawberry banana pudding my family already loves, swapping Nilla wafers for something a little richer.

What is Chessmen Strawberry Banana Pudding?

So, what’s the deal with this specific banana pudding? Well, traditional banana pudding uses vanilla wafers, right? This version swaps those out for Pepperidge Farm Chessmen cookies – those elegant, buttery shortbread-style cookies. They bring a richer, less sweet, and distinctly buttery flavor that totally elevates the whole dish. Mixed with creamy vanilla pudding, sweet bananas, and bright strawberries, it creates this amazing texture contrast. It’s a popular twist for a reason! While we’re using instant pudding for speed here (because, life!), if you’re feeling ambitious and want a truly from-scratch experience, Sally’s Baking Addiction has a fantastic guide to homemade vanilla pudding that would be divine. This banana pudding with chessmen cookies recipe is all about that simple, elegant upgrade.

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Why This Recipe Works

Okay, here’s why this version gets rave reviews in my house (and everywhere I take it!):

• The Chessmen Factor: Seriously, these cookies make a difference. Their buttery flavor and slightly firmer texture hold up beautifully against the creamy pudding and fruit. It’s a game-changer.
• No-Bake Bliss: Did I mention NO OVEN REQUIRED? Mamma mia, that’s music to my ears, especially during warmer Portland months or busy weeknights.
• Crowd-Pleaser: It looks impressive layered in a dish and tastes even better. Expect requests for the recipe! It’s as reliably delicious as my go-to strawberry banana cheesecake salad.
• Strawberry Sunshine: Adding strawberries cuts the richness and adds a lovely freshness that balances the sweet bananas and buttery cookies.
• Easy Peasy: If you can layer ingredients in a dish, you can make this Chessmen banana pudding. I’ve taught my 10-year-old how to assemble it – it’s that straightforward.

Ingredients

What You’ll Need

Gather ’round, pantry wizards! Here’s your shopping list:

• Pepperidge Farm Chessmen Cookies: Two (7.25 oz) bags. These are the stars! Don’t substitute if you want that signature flavor. Using specific branded cookies like this always feels a bit fun, kind of like when folks get creative making that viral Subway footlong cookie at home.
• Instant Vanilla Pudding Mix: Two (3.4 oz) boxes. Jell-O brand works great.
• Cold Milk: 3 cups. Whole milk for ultimate creaminess.
• Sweetened Condensed Milk: One (14 oz) can. The secret weapon for richness! Eagle Brand is my usual pick.
• Vanilla Extract: 1 tsp. Just a splash for extra flavor depth.
• Cool Whip or Whipped Cream: One (8 oz) container, thawed. Or whip up about 2 cups of your own heavy cream.
• Fresh Bananas: 4-5 medium, ripe but firm, sliced.
• Fresh Strawberries: 1 lb (about 2 pints), hulled and sliced. Adds that essential pop of color and freshness.

Ingredient Swaps

Need to make a change? No problem:

• Cookies: While Chessmen are key for this specific recipe, if you absolutely can’t find them, other buttery shortbread cookies (like Walkers) are the closest substitute. Nilla wafers work for a traditional texture. The goal is finding the best cookies for banana pudding that offer that buttery richness.
• Pudding: Feel free to use French Vanilla instant pudding for a deeper flavor, or make your own vanilla pudding from scratch if you have the time.
• Fruit: You can omit the strawberries for a pure Chessmen banana pudding experience, or swap strawberries for raspberries or peaches. If you go all strawberry, it’s closer to my simple strawberry pudding, but with Chessmen!
• Dairy-Free: Use dairy-free pudding mix, plant-based milk (oat or cashew work well), coconut condensed milk, and dairy-free whipped topping. The Chessmen cookies do contain butter and milk, so this swap only works if you also substitute the cookies for a dairy-free/vegan shortbread alternative.

How to Make Chessmen Strawberry Banana Pudding

Step-by-Step Instructions

Alright, let’s assemble this beauty. Grab your dish (9×13 inch or a trifle bowl works great!) and let’s layer:

1. Whip up the Pudding: In a large bowl, whisk the instant pudding mix and cold milk for about 2 minutes until it starts thickening.
2. Make it Creamy: Whisk in the sweetened condensed milk and vanilla extract until smooth.
3. Fold in the Fluff: Gently fold in the thawed Cool Whip or whipped cream. Try not to deflate it! Set aside.
4. First Layer: Spread a very thin layer of the pudding mixture on the bottom of your dish.
5. Chessmen Layer 1: Arrange a single layer of Chessmen cookies over the pudding. Cover the bottom completely.
6. Fruit Layer 1: Top the cookies with a layer of sliced bananas, then a layer of sliced strawberries.
7. Pudding Layer 1: Spread about half of the remaining pudding mixture over the fruit.
8. Chessmen Layer 2: Add another full layer of Chessmen cookies.
9. Fruit Layer 2: Layer the remaining sliced bananas and strawberries over the cookies. Sometimes adding just one extra special ingredient makes all the difference, kind of like figuring out what to add to macaroni and cheese to make it amazing!
10. Final Pudding Layer: Spread the rest of the pudding mixture evenly over the top.
11. Chill Time!: Cover tightly with plastic wrap, pressing it gently against the surface. Refrigerate for at least 4-6 hours, but overnight is even better. This allows the cookies to soften slightly and the flavors to meld perfectly for the best pepperidge farm banana pudding recipe experience.

Serving Suggestions

• Garnish: Top with extra whipped cream, a few strategically placed Chessmen cookies (maybe standing up?), and fresh strawberry slices before serving.
• Keep Cool: Serve chilled directly from the refrigerator.
• Big Scoops: Ensure each serving gets all the layers – cookie, fruit, and creamy pudding!

Ways to Enjoy Chessmen Strawberry Banana Pudding

This dessert fits in anywhere:

1. Potluck Superstar: Guaranteed to be one of the first dishes emptied.
2. Holiday Treat: Perfect for Easter, Mother’s Day, or summer BBQs. It’s one of those universally loved dessert recipes.
3. Make-Ahead Marvel: Ideal for entertaining since you have to make it ahead.
4. Comfort Food Hug: Sometimes, you just need a bowl of creamy, buttery goodness.

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Time-Saving Tips

Keeping it quick and easy!

Shortcuts

• Pudding Prep: Make the pudding mixture (steps 1-3) up to a day ahead and store it covered in the fridge.
• Cookie Placement: Don’t overthink the cookie arrangement – just get them in a single layer.

Pro Tips

• Firm Bananas: Use ripe bananas that are still firm to avoid a mushy texture. Slice just before layering.
• Don’t Skip Chilling: This is CRUCIAL. The chilling time allows the Chessmen cookies to soften just enough to be scoopable while retaining some buttery texture. Trust me on this one!
• Gentle Folding: Be gentle when folding in the whipped topping to keep the pudding light and airy.

Storage and Freezing Tips

• Fridge: Store leftovers tightly covered in the fridge for up to 3 days. The cookies will continue to soften over time.
• Freezer: Like most banana puddings, this doesn’t freeze well. The texture changes upon thawing. Best enjoyed fresh!

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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.

Print Recipe Pin Recipe

Prep Time 25 minutes mins

Chilling Time 4 hours hrs

Total Time 4 hours hrs 25 minutes mins

Servings: 12

Course: Dessert

Cuisine: American, Southwestern

Calories: 500

Ingredients Equipment Method Notes

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

Equipment

• Large bowl
• Whisk
• Measuring Cups
• Measuring spoons
• 9×13 inch Baking Dish or Trifle Bowl
• Knife
• Cutting Board
• Spatula or Large Spoon
• Plastic Wrap

Method

 

1. Whip up the Pudding: In a large bowl, whisk the instant pudding mix and cold milk for about 2 minutes until it starts thickening.
2. Make it Creamy: Whisk in the sweetened condensed milk and vanilla extract until smooth.
3. Fold in the Fluff: Gently fold in the thawed Cool Whip or whipped cream until just combined.
4. First Layer: Spread a very thin layer of the pudding mixture on the bottom of a 9×13 inch baking dish or trifle bowl.
5. Chessmen Layer 1: Arrange a single layer of Chessmen cookies over the pudding, covering the bottom.
6. Fruit Layer 1: Top the cookies with a layer of sliced bananas, then a layer of sliced strawberries.
7. Pudding Layer 1: Spread about half of the remaining pudding mixture over the fruit.
8. Chessmen Layer 2: Add another full layer of Chessmen cookies.
9. Fruit Layer 2: Layer the remaining sliced bananas and strawberries over the cookies.
10. Final Pudding Layer: Spread the rest of the pudding mixture evenly over the top.
11. 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

Frequently Asked Questions

Let’s tackle some common questions about this beauty:

Final Thoughts

And there you have it – your new go-to impressive-but-easy dessert! This Chessmen banana pudding with strawberries is a guaranteed hit. The buttery cookies truly make it something special, and the ease of putting it together? Chef’s kiss! It’s fancy enough for company but simple enough that you’ll find excuses to make it just because. If you loved the original strawberry banana pudding, give this elevated version a try! Let me know if you whip this up – leave a comment below! Buon appetito!