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Strawberry Shortcake Whoopie Pies

Close-up of strawberry shortcake whoopie pies tied with kitchen twine

So I didn’t get a lot of sleep last night…

Like I’m pretty tired.

You wanna know why?  Because things seem impossibly ridiculous at 2:00 am.  I mean, any issue you might be having in your life, thinking about it at 2:00 am will make it the hugest, largest, most insurmountable problem you have ever had.  Ever.

So I laid awake from 2:00 am – 4:00 am thinking about the very important matter of my kid’s iPods.  I had myself convinced in the wee hours that by allowing them to play their iPods frequently, I was turning their brain into liquid, damaging their vision, preventing them from ever getting into college, getting a girlfriend or getting married, which consequently lowered the possibility of me ever having grandchildren.  All because they play their iPods.

I was basically a sweaty, panicked wreck.

How I got from point A to point B on that matter is far too long and nonsensical a story to tell you here and now, but I will tell you should disregard your brain-talk at 2:00 am.  It exaggerates.  And dramatizes…and hyperbolizes every scenario in your life.

BUT sometimes, on rare occasion, in between thoughts of Minecraft and failure to launch scenarios, accompanied by images of being an old angry woman with no grandchildren to speak of, you get a glimmer of a good idea.

Which leads me to today’s recipe.

Thanks 2:00 am brain.

Strawberry Shortcake Whoopie Pies.

Strawberry Shortcake Whoopie Pies | Cookies and Cups
Shortcake whoopie pie batter on a stand mixer blade
Circles of Shortcake whoopie pie batter on a baking mat
Half of a vanilla whoopie pie with whipped cream filling
An open-faced shortcake whoopie pie topped with whipped cream and strawberry slices

You just start by making a simple vanilla batter…
Drop spoonfuls of the batter onto a parchment lined baking sheet and then flatten the batter out. It’s pretty thick, so you need to flatten it, otherwise they will be way too tall after they bake…
When they are done and cooled, spread some yummy filling on one side. I used a butter based filling. I tried using a whipped cream filling and it didn’t work. While delicious, it squished out the sides and was very un-whoopie pie-like.
Then top the filling with sliced strawberries.
Really stuff as many slices as you can mange in there!

Strawberry Shortcake Whoopie Pies | Cookies and Cups

Then eat the heck of it…

Strawberry Shortcake Whoopie Pies | Cookies and Cups
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Strawberry Shortcake Whoopie Pies

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Makes 12 whoopie pies




  • 1 cup butter, room temperature
  • 1 1/2 cups sugar
  • 1 tsp salt
  • 1 Tbsp baking powder
  • 3 eggs
  • 4 1/4 cups flour
  • 1 cup milk
  • 1 Tbsp vanilla


  • 10 Tbsp butter, room temperature
  • 1 tsp vanilla
  • 4 Tbsp heavy cream
  • 2 1/23 cups powdered sugar
  • 1 pint strawberries, sliced thinly


  1. Preheat oven to 400°
  2. Line baking sheet with parchment paper.
  3. Cream together butter and sugar for approx 1 minute on medium speed with your mixer.
  4. Turn mixer to low and add in baking powder, salt and eggs. Turn mixer back up to medium and mix until smooth.
  5. Mix vanilla into your milk.
  6. With your mixer on low, alternate adding the flour and the milk/vanilla mixture, starting and ending with flour. Mix until just combined.
  7. Drop dough by heaping tablespoon onto prepared baking sheet about 2 inches apart, flatten the dough, so it’s not so rounded.
  8. Bake 10-11 minutes until edges are golden and tops are set.
  9. Transfer to wire rack to continue cooling.


  1. Cream butter in mixer with vanilla about 2 minutes. Slowly add in 2 1/2 cups powdered sugar and cream, beating for 2-3 minutes more. Add more powdered sugar if you desire a thicker consistency.


  1. Spread about 2 Tbsp of filling on the bottom of a cookie, top with 5-6 strawberry slices. Spread a teaspoon of filling on the bottom of the other cookie (to help stick) and press the cookie together forming a sandwich.

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43 comments on “Strawberry Shortcake Whoopie Pies”

  1. I have those 2 am thoughts too…
    But on the positive side, the whoopie pies look amazing, and I don’t even normally like whoopie pies. Yum!

  2. Loretta | A Finn In The Kitchen

    I’m waiting for the invention that allows you to turn your brain off at night! It would be so pleasant…

    But, yeah. I want these so bad! Probably even better with peak summer berries. They look comforting. Is that weird?

  3. Karen @ Sugartown Sweets

    Haha! My kids are @ 2:am, I am dreaming up new sweets! These are simply beautiful. 🙂

  4. These look absolutely amazing. I am making these for my sisters birthday on February 18th, she loves both Whoopie Pies and Strawberry Shortcake, these are perfect.

    About the 2:00 am brain, I am so glad this happens to other people and its not just me being crazy, in the morning it seems absolutely ridiculous but in the middle of the night it’s so real.

  5. How creative! i`m loving this idea. 🙂 I`m awake at 2am too, but studying, instead. I don`t wish to be awake at 2…but I guess it happens to people.

    Also, have faith your children will turn out fine and you`ll have grandchildren. Even if they`re attached to their ipods.

  6. Well, this is happening in my life. Like, soon.

    My 2am brain last night was…well, you wouldn’t even believe me. Suffice it to say, I’m apparently starring in a LIfetime Movie right now. Which makes for awesome 2am-4am thoughts, as you can imagine.

  7. Liz @ Tip Top Shape

    Oh my word, that first picture is adorable. I love baked goods being outfitted like gifts — too cute! Anyhoo, these look delicious!

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