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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. Why the string holding the whoopie pie together? They should stack without it. Personally, I don’t think the string adds anything to what appears to be an addictive goodie. But, that’s me.

    2 am brain – my 2 am brain tends to rehash all the things that have bothered me during the day. If I decide during the day to restrict the use of IPods, then at 2am, I get to remake the decision and go over all the arguments pro and con on the issue, including some my conscious brain ignored. Go figure πŸ™

  2. Emily ~SoDomesticated~

    Oooo yum… these look delectable!

    I totally sabotage my sleep by thinking of stuff in the middle of the night while trying to fall asleep. I think it’s a woman thang…

  3. Carla @ Carlas Confections

    Haha yes! Oh the 2am brain… hardly ever anything good comes out of them… but im so glad these did πŸ™‚

  4. Jess @ On Sugar Mountain

    These are beautiful!! I’m glad one good idea came out of 2am brain πŸ™‚ I’ve definitely had my share of those at college (aka how will I pass my classes, get a good job etc etc ’til I’m spiraling into ideas about becoming a crazy cat lady).

  5. For me it’s not really 2AM but just thinking about anything serious before i go to sleep. Which then prevents me from falling asleep for approximately a whole hour. Such a useless time suck!

    I am so ready for strawberries. Love these whoopies!

  6. vanillasugarblog

    2am brain is the worst because you know you’re turning your brain into mush by not sleeping enough. I am the extreme worrier!

  7. My crazy brain happens at 4:30 am. Last three mornings. Why oh why can’t I sleep until 6!? I’ll be thinking about these whoopie pies tomorrow.

  8. Annie @ Annie's Noms

    These are adorable! πŸ˜€ I totally get the 2am brain thing, sometimes I almost can’t believe the things I think up, but at least you got the idea for these! I absolutely adore strawberries and shortcakes, not had whoopie pies yet, but that’s sure going to change soon! πŸ™‚

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