
I can't get enough of these chocolatey whoopie pies every December. They're soft cookies stuffed with fluffy marshmallow and finished off with peppermint crunch. They're always gone before I can blink. My kids and I have so much fun baking them together. Folks love getting these as gifts, and they're a hit at every holiday get-together or cookie swap we bring 'em to.
Top Choice for Festive Fun
These treats really nail that holiday feeling. The cookies come out so cakey and tender, and the filling's light as a cloud. The crushed candy canes add a crisp, peppermint-y pop that makes 'em extra special. You can totally shake things up and toss on sprinkles or swap in cream cheese frosting if you're after something new. No matter what, they're always a crowd-pleaser.
What You Gotta Have
- Sour Cream: About half a cup keeps the cookies soft and rich.
- Baking Soda: A teaspoon gives the cookies their awesome texture.
- Baking Powder: Just a teaspoon helps them puff up nicely.
- Shortening: Half a cup goes in for structure—don't skip it.
- Egg: One big egg, make sure it's not cold.
- Powdered Sugar: A cup sweetens and thickens your filling.
- Brown Sugar: Pack in a cup to give the cookies that caramel-y goodness.
- Unsalted Butter: Use half a cup, get it super soft first.
- Hot Water: Just enough to smooth things out.
- Salt: Half a teaspoon brings out all the flavors.
- All-Purpose Flour: Two cups, sift so your dough's nice and airy.
- Vanilla Extract: Add a teaspoon for that hit of flavor.
- Unsweetened Cocoa: A third of a cup brings all the deep chocolate notes.
- Crushed Candy Canes: Smash 'em up for that cool finish.
- Marshmallow Fluff: Grab a 7-ounce jar for the filling.
Fun and Easy Step-By-Step
- Get the Filling Ready
- Beat up your shortening and powdered sugar until smooth, then gently mix in the marshmallow fluff. If it feels too thin, throw in a little more powdered sugar till it thickens up just right.
- Shape and Bake
- Scoop out about a quarter cupful of dough onto prepped baking sheets. Pat the tops gently with a spatula that you've oiled up. Bake at 350°F for 10 to 12 minutes, then let 'em cool all the way.
- Blend Your Wet Mix
- In your mixer, whip together the brown sugar, shortening, and butter till it's light and fluffy. Toss in your egg and the vanilla, then blend until it's all smooth and happy.
- Prep the Chocolate Paste
- Blend cocoa and baking soda in a bowl. Splash in enough hot water to make it silky, then stir the sour cream in. Put it aside for now.
- Dry Ingredients Set
- Whisk up your flour, baking powder, and salt in another bowl so they're all combined.
- Mix It All Together
- Pour in half your dry mix, then your chocolate blend, and finish with the rest of the dry stuff. Mix it up but don't go overboard—just till it comes together.
- Put the Cookies Together
- Spread the marshmallow filling on half the cookies. Top them off with the rest, then roll the sides through crushed candy canes so they're coated in that peppermint crunch.
Twist Things Your Way
Want to switch things up? Swap the peppermint for colorful sprinkles if you need a birthday vibe. If you're short on time, go store-bought with the frosting. Tiny versions make awesome bite-sized party bites, too—your guests will love the mini size.

Keep 'Em Delicious
Just pop these in a tight container and chill in the fridge—they'll hold up fine for a whole week. To serve, let 'em come back to room temp for best flavor. Need to make a bunch in advance? Freeze without the peppermint for up to half a year and roll in candy canes once thawed, so the crunch stays perfect every time.
Common Questions
- → Can I use other toppings besides candy canes?
Totally! Crush up some chocolate, toss on sprinkles, or use bits of peppermint bark for a twist.
- → How can I keep these fresh?
Stash them in a sealed container in your fridge. They'll stay happy for five days.
- → Is it possible to freeze these?
Freeze just the cookies (before adding filling and peppermint) for up to two months. Pull them out when you need, then fill and finish.
- → Why is my marshmallow filling runny?
The filling might be too warm. Pop it in the fridge so it thickens up before you use it.
- → Can I prep any part in advance?
Go ahead and bake the cookies ahead of time. Finish with filling and peppermint right before serving for the freshest bite.