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Festive Chocolate Sandwich Treats

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These holiday whoopie pies combine rich chocolate cookies with sweet marshmallow filling, finished with crushed candy canes for a festive touch. Perfect for Christmas cookie exchanges.

Casey
Updated on Mon, 20 Jan 2025 20:06:36 GMT
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A close-up of chocolate whoopie pies filled with white cream and topped with crushed peppermint pieces, set against a festive background. Pin it
A close-up of chocolate whoopie pies filled with white cream and topped with crushed peppermint pieces, set against a festive background. | cookingwithcasey.com

Let me share my absolute favorite holiday treat that brings back the sweetest memories of baking with my kids. These Christmas Whoopie Pies are pure magic soft chocolatey cookies sandwiched with fluffy marshmallow filling and rolled in crushed candy canes. Every time I make these they disappear faster than Santa down a chimney. They're perfect for cookie swaps family gatherings or wrapped up as homemade gifts that everyone loves.

Why These Are My Holiday Go-To

What makes these whoopie pies extra special is how they combine everything we love about the holidays. The cookies are perfectly soft and cakey while the marshmallow filling is cloud-like fluffy. Add that festive crunch from crushed candy canes and you've got something truly magical. I love how versatile they are too sometimes I'll switch things up with holiday sprinkles or cream cheese frosting depending on what my family's craving.

What You'll Need in Your Kitchen

  • Unsweetened Cocoa: You'll need ⅓ cup for that perfect chocolate flavor.
  • Baking Soda: Just 1 teaspoon this works with the cocoa to make magic happen.
  • Hot Water: Just enough to make everything smooth.
  • Sour Cream: ½ cup this makes our cookies super moist.
  • All-Purpose Flour: 2 cups sifted to keep things smooth.
  • Baking Powder: 1 teaspoon for the perfect rise.
  • Salt: ½ teaspoon trust me it makes everything taste better.
  • Brown Sugar: 1 cup packed for that caramel note.
  • Shortening: ½ cup this gives our cookies structure.
  • Unsalted Butter: ½ cup nice and soft.
  • Egg: 1 large room temperature is important.
  • Vanilla Extract: 1 teaspoon for flavor.
  • Marshmallow Fluff: One 7 oz jar for that dreamy filling.
  • Powdered Sugar: 1 cup to make the filling just right.
  • Crushed Candy Canes: For that festive peppermint magic.

Let's Make Some Holiday Magic

Start with the Chocolate Base
Mix your cocoa and baking soda in a bowl pour in just enough hot water to make a smooth paste then stir in that sour cream until it's perfect. Set this aside it's going to make our cookies amazing.
Get Your Dry Team Ready
In another bowl whisk together your flour baking powder and salt. This is our dry dream team.
Make Things Fluffy
Now in your mixer beat that brown sugar shortening and butter until it's super fluffy. Add your egg and vanilla and keep mixing until everything's happy together.
Bring It All Together
Add half your flour mix then that chocolate mixture then finish with the rest of your flour. Mix just until it's smooth we don't want to overdo it.
Shape Those Cookies
Use a ¼ cup to scoop the dough onto your lined baking sheets give them a gentle pat with an oiled spatula then into the 350°F oven they go for 10-12 minutes. Let them cool completely.
Make That Dreamy Filling
Beat your shortening and powdered sugar then add the marshmallow fluff until it's perfectly smooth and fluffy. If it needs thickening add a bit more powdered sugar.
Put Them Together
Here's the fun part spread that filling on half your cookies top with the others then roll the edges in crushed candy canes. Pure holiday happiness.

Mix It Up Your Way

Want to make these your own? Try rainbow sprinkles instead of candy canes for birthday parties. Sometimes when I'm in a rush I'll use cream cheese frosting from the store (it's our little secret). You can even make the cookies smaller for bite-sized treats perfect for holiday parties.

A close-up of chocolate whoopie pies filled with cream and topped with crushed peppermint candies, displayed on a white plate. Pin it
A close-up of chocolate whoopie pies filled with cream and topped with crushed peppermint candies, displayed on a white plate. | cookingwithcasey.com

Keeping Them Fresh

Pop these beauties in an airtight container in the fridge they'll stay perfect for a week. Just let them warm up a bit before serving. Planning ahead? You can freeze them for up to six months just wait to add the candy cane coating until after they thaw. Trust me it keeps that minty crunch just right.

Frequently Asked Questions

→ Can I make these ahead of time?

Yes, bake the cookies ahead and store unfilled. Add filling and candy canes just before serving for best results.

→ Why is my filling too soft?

If the filling is too soft, chill it in the fridge until it firms up enough to work with.

→ Can I freeze these whoopie pies?

Freeze unfilled cookies for up to 2 months. Add filling and candy canes after thawing.

→ How should I store these?

Keep in an airtight container in the fridge for up to 5 days.

→ Can I use different candy toppings?

Yes, try crushed peppermint bark, chocolate chips, or holiday sprinkles instead of candy canes.

Christmas Whoopie Pies

Soft chocolate sandwich cookies filled with fluffy marshmallow cream and rolled in crushed candy canes. A perfect holiday treat that's sure to impress.

Prep Time
25 Minutes
Cook Time
14 Minutes
Total Time
39 Minutes
By: Casey


Difficulty: Intermediate

Cuisine: American

Yield: 6 Servings (6)

Dietary: Vegetarian

Ingredients

01 ⅔ cup unsweetened cocoa powder.
02 1 teaspoon baking soda.
03 ½ cup sour cream.
04 2 cups all-purpose flour.
05 1 teaspoon baking powder.
06 ¾ teaspoon salt.
07 1⅓ cups light brown sugar.
08 ¼ cup vegetable shortening.
09 ¼ cup unsalted butter, softened.
10 1 large egg.
11 2 teaspoons vanilla extract.
12 ⅓ cup vegetable shortening.
13 ⅓ cup unsalted butter, softened.
14 1 tablespoon light corn syrup.
15 2 teaspoons vanilla extract.
16 1 cup powdered sugar.
17 1 pinch salt.
18 1 (7 oz) jar marshmallow creme.
19 6 candy canes, crushed.

Instructions

Step 01

Preheat oven to 350°F.

Step 02

Mix cocoa powder and baking soda, add hot water to make paste.

Step 03

Stir in sour cream until combined.

Step 04

Mix flour, baking powder and salt separately.

Step 05

Beat brown sugar, shortening and butter until fluffy.

Step 06

Add egg and vanilla.

Step 07

Add flour mix and cocoa mix alternately.

Step 08

Drop ¼ cup portions onto lined baking sheets.

Step 09

Smooth tops with greased spatula.

Step 10

Bake 12-14 minutes.

Step 11

Cool completely.

Step 12

Beat shortening, butter, corn syrup, vanilla, sugar and salt.

Step 13

Mix in marshmallow cream.

Step 14

Spread filling on half the cookies.

Step 15

Top with remaining cookies.

Step 16

Roll edges in crushed candy canes.

Notes

  1. Classic whoopie pies with a holiday twist.
  2. Chill filling if too soft to work with.
  3. Can make cookies ahead and fill just before serving.

Tools You'll Need

  • Stand mixer.
  • Glass mixing bowls.
  • Whisk.
  • Non-stick baking sheets.
  • Parchment paper.
  • Wire cooling rack.

Allergy Information

Please check ingredients for potential allergens and consult a health professional if in doubt.
  • Dairy (butter, sour cream).
  • Eggs.
  • Wheat (flour).

Nutrition Facts (Per Serving)

It is important to consider this information as approximate and not to use it as definitive health advice.
  • Calories: 930
  • Total Fat: 43 g
  • Total Carbohydrate: 138 g
  • Protein: 7 g