Chocolate Chip Whoopie Pies with Strawberry Whipped Cream Filling

I feel like it’s been forever since we’ve done a dessert post. It probably hasn’t even been a full week, but still…I’m going through withdrawls. Valentine’s day is right around the corner and it is high time we post some sweet treats for your sweetie.

I am really happy with how these Whoopie Pies turned out. Chocolate Chip Whoopie Pies with Strawberry Whipped Cream Filling. Need I say more?

Ok, I’ll say more. I was slightly scared about trying to form these into hearts, but with the help of a cookie cutter it was really simple. They held their shape and baked perfectly, just slightly golden. They turned out adorable if I do say so myself. And I do.

But more importantly they tasted really good too. I’ve always been a fan of strawberries in my desserts. They add a pop of color and an extra dose of sweetness, which I heart. Taste…a 10, presentation…a 10, creativity…a 10. The judges rule they’re perfect.

Also…Jen gave me the Whoopie Pie book pictured below for Christmas and I’m finally getting around to using it. There are lots of fun and creative things that I can’t wait to try!! Thanks Jen :)

Here’s what you’ll need

Start by creaming together butter, shortening and both sugars

In a small bowl sift together flour, baking powder and salt. Set aside

Add the eggs and buttermilk and beat until combined

In a measuring cup combine the milk, vinegar and baking soda

Add milk mixture as well as the dry flour mixture and beat until just combined

In goes the vanilla, mix until completely combined then fold in the mini chocolate chips

We used a heart shaped cookie cutter to form heart shaped whoopie pies. Pop those in the oven

Using the whisk attachment beat cream until you form firm peaks. Carefully fold in the confectioners’ sugar

Carefully fold in the strawberry jelly too

Assemble the whoopie pies by spreading filling on the flat side of cakes and sandwiching sliced strawberries in the center

These turned out so cute!

And they taste good too! A fun Valentine’s Day treat for your sweetie!


Chocolate Chip Whoopie Pies with Strawberry Whipped Cream Fillling
Yields 16
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Total Time
1 hr
Total Time
1 hr
For the Cakes
  1. 2¼ cups all-purpose flour
  2. 1½ teaspoons baking powder
  3. ½ teaspoon salt
  4. 4 tablespoons unsalted butter, at room temperature
  5. 4 tablespoons vegetable shortening
  6. ½ cup sugar
  7. ½ cup packed brown sugar
  8. 2 large eggs
  9. ½ cup buttermilk
  10. 2 tablespoons milk
  11. 1 teaspoon baking soda
  12. 1 teaspoon white vinegar
  13. ½ teaspoon vanilla
  14. 1 cup mini chocolate chips
For the Filling
  1. 1¼ cups heavy cream
  2. 4 tablespoons confectioners’ sugar
  3. 3 tablespoons strawberry jelly
  4. 1 cup sliced strawberries
  1. Preheat the oven to 375 degrees F.
  2. Line 2 baking sheets with parchment paper.
  3. In a small bowl, sift together the flour, baking powder and salt. Set aside.
  4. In the bowl of a stand mixer fitted with the paddle attachment, beat the butter, shortening, sugar and brown sugar until light and creamy, about 3 minutes.
  5. Add the eggs and the buttermilk and beat until combined.
  6. In a measuring cup, combine the milk, baking soda and vinegar.
  7. Add the milk mixture to the batter along with the sifted flour mixture and beat on low speed until just combined.
  8. Add the vanilla then beat on medium speed for about 2 minutes, or until completely combined. Fold in the mini chocolate chips.
  9. Using a spoon, drop about 1 tablespoon of batter at a time onto the baking sheets.
  10. Space them at least 2 inches apart.
  11. If you want heart shaped whoopie pies, use a small heart shaped cookie cutter to form a heart shape then carefully pull the cutter away leaving the batter in a heart shape.
  12. Or use a whoopie pie pan with heart molds.
  13. Bake 1 sheet at a time for about 10 minutes, or until the cakes have just started to brown. Remove from the oven and let the cakes cool on the baking sheet for at least 5 minutes before transferring them to a cooling rack.
  14. To make the filling, pour the heavy cream into the bowl of a stand mixer fitted with the whisk attachment.
  15. Beat until it forms firm peaks.
  16. Carefully fold in the confectioners’ sugar and the jelly.
  17. To assemble the whoopie pies, spread the filling on the flat sides of 2 cakes.
  18. Top with 3 or so sliced strawberries and place the other whoopie pie on top.
  19. You’ll want filling on both of the whoopie pies to act like a glue.
Adapted from Cakes from Whoopie Pies by Sarah Billingsley
Adapted from Cakes from Whoopie Pies by Sarah Billingsley


  1. says

    I never think to use my cookie cutouts for chocolate chip cookies. I mean…why not?!?! Super cute whoopies you got here.

    By the way, your baked brie would be a perfect addition to my list of Super Bowl snacks. Hope you’ll swing by and join Dipstock. :)

  2. Eric says

    Do you think instead of using cream for the filling, I could use vanilla ice cream? How would I do that? My girlfriend & I are trying this genius idea Sunday but aren’t fans . of the cream . Thanks!

    • says

      Eric, I would spread a thin layer (maybe 1/2 inch) of ice cream in a baking dish. Freeze it then use a heart shaped cookie cutter to cut out the ice cream. I think it is a great idea! Let me know if it works out!

  3. says

    Just made this recipe and it was amazing! Perfect for those who enjoy deserts that are not too rich or sweet. Overall, my entire family is very happy with me tonight.


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