Strawberry Shortcake Whoopie Pies

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

You just start by making a simple vanilla batter…
Shortcake whoopie pie batter on a stand mixer bladeDrop 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…
Circles of Shortcake whoopie pie batter on a baking matWhen 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.
Half of a vanilla whoopie pie with whipped cream fillingThen top the filling with sliced strawberries.
An open-faced shortcake whoopie pie topped with whipped cream and strawberry slicesReally stuff as many slices as you can mange in there!

Strawberry Shortcake Whoopie Pies | Cookies and CupsThen eat the heck of it…

Strawberry Shortcake Whoopie Pies | Cookies and Cups


Strawberry Shortcake Whoopie Pies


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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Hi! I’m Shelly and I’m an addict. Of the buttercream sort. I started this site a few years ago as a way to justify my sugary, buttery obsession with desserts. It has worked out well for me so far, because as it turns out you guys all love sugary, buttery desserts too! It feels good to know you're not alone, doesn’t it?

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Apr 17, 2013 8:23 pm

Omg! These are so yummy! The cookie is Devine

Apr 10, 2013 5:44 pm

Wowzers….Could I possibly do these with a simple whipped cream filling (double Swiss cream for stiffness)…instead of the buttercream ..without damaging your recipe?…Sadly…the husband is not a “fan” of frosting…but loves whipped cream. I would love them in any form! Thank you for a perfect offering , now that the huge beautiful strawberries from Spain are everywhere in the outdoor markets here in France. I adore Strawberry Shortcake!

Feb 18, 2013 10:12 am

Whoopie pies are on my A list and beautifully created.

Feb 6, 2013 12:39 pm

Beautiful photos! And amazing blog!

Feb 2, 2013 10:29 pm

Oh my…..STOP IT =) This looks and sounds amazing!!

Feb 1, 2013 3:17 pm

These look so cute and girly and absolutely scrumptious! Great recipe!

Feb 1, 2013 10:27 am

at least something awesome also came out of 2am brain. wow!!!! these look yum. cant wait to try them!!

Feb 1, 2013 10:05 am

I bought 80 million yards of bakers twine off Pick Your Plum (hate to love that site!!!). I want to make these just so I can tie bakers twine around them. So cute. 😉

They look delicious too, I love strawberry shortcake and sure could use a taste of summer!

Feb 1, 2013 9:50 am


There is nothing I love more than Strawberry shortcake.

Feb 1, 2013 4:01 am

Oh glory be! Please do stay awake more often if that is what you are going to whip up! Lol! Looks delicious!!!

Feb 1, 2013 3:52 am

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!

Feb 1, 2013 12:06 am

These look amazing!!!!!!!!!!!!!!

Feb 1, 2013 12:03 am

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?

Jan 31, 2013 10:20 pm

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

Jan 31, 2013 10:13 pm

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.

Shelly Hi! I’m Shelly and I’m an addict. Of the buttercream sort. I started this site a few years ago as a way to justify my sugary, buttery obsession with desserts. It has worked out well for me so far, because as it turns out you guys all love sugary, buttery desserts too! It feels good to know you're not alone, doesn’t it?

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