Strawberry Shortcake Whoopie Pies

Disclosure: I received coupons from Driscoll’s Berries in order to develop a recipe for their Strawberry Shortcake contest. All photos and opinions remain my own.

I am a whoopie pie freak. What’s my favorite pie? Whoopie. Cupcakes for a classroom birthday party? Nope, whoopie pies. Going to a picnic? I already know what I’m making. I have a reputation for bringing the whoopie to the party. And so it only seemed natural that when I received the challenge to develop a strawberry shortcake recipe for Driscoll’s Berries, the first thing I thought of was not biscuits or pound cake, but how I could create a Strawberry Shortcake Whoopie Pie.

Strawberry Shortcake Whoopie Pies - poet in the pantry

I spent at least a week considering how I would pull off this culinary masterpiece. Macerated or compote? Traditional filling or Italian meringue? Vanilla or chocolate? When I thought I finally figured it out, I set to work.

The compote was the first step, and really it’s quite easy. Just let the berries simmer in some sugar and wine, then thicken with more wine, Cointreau (or orange-flavored liqueur), and cornstarch. The resulting compote is more than you’ll need for the whoopie pies, but the proportions work out better than halving the recipe–who wants to work in half Tablespoons, anyway? So stash the rest in the fridge and I’m sure you’ll find plenty of other uses for it. Or just eat it with a spoon. That works, too.

Strawberry Shortcake Whoopie Pies - poet in the pantry

Next, I set out to make the best vanilla whoopie cakes/cookies ever. Vanilla whoopie pies are nothing new to me, but I wanted to improve on my previous attempt. I left behind the buttermilk in favor of the more mild whole milk and upped the granulated sugar content. When the first batch emerged from the oven, I nearly swooned–they were exactly as I envisioned! That so rarely happens! I was on a roll!

Strawberry Shortcake Whoopie Pies - poet in the pantry

Given my track record thus far, I should have known the third component would be problematic. And it was. I had settled upon Italian meringue for my filling, a marshmallowy, Fluff-like filling that would class this up a bit. But I’ve never prepared Italian meringue before. My first attempt ended up with clumps of cornstarch in the egg whites and no real success in them doing anything other than going for a spin around the bowl for 5 or so minutes. I cleaned the mixer bowl, dried it thoroughly, and tried again with cold egg whites. Perhaps the other ones were too warm? While I had the stand mixer whisking away, I tried to make the sugar syrup on the stove. It was not my best moment in multi-tasking. The syrup should have cooked to soft ball stage (around 238 degrees Fahrenheit). I stepped away for a moment, checking on the egg whites, and when I returned I found my syrup had reached soft crack stage instead (around 270 degrees Fahrenheit). Crud!!! The egg whites, by the way, would do no more than foam lightly, even after whisking at full 10 speed for more than 7 minutes. They never did form peaks of any sort, soft or otherwise. I’m not one to give up easily, but I did. I wasn’t sure how many more tries Italian meringue would take, but it wasn’t important enough to me to keep going. Not this time. And so, the third component became whipped cream. Which is more traditional anyway, so that works out for the best, right?

Strawberry Shortcake Whoopie Pies - poet in the pantry

Whoopie pies usually are portable, hand-held snacks, requiring no cutlery or dishware for enjoyment. Strawberry Shortcake Whoopie Pies, on the other hand, are a little messier. They need to be assembled immediately before serving. And you’ll probably end up with a trail of strawberry compote down your arm if you try walking around with them. Not that that’s a bad thing… just fair warning so you won’t look like you survived a zombie attack. Still, the whoopie cakes/cookies make a great change from the traditional biscuits and dessert shells, and the cuteness factor cannot be beat. They’re not exactly as I planned, but I’m pretty happy with the end result. And I heard no complaints from my taste testers. That’s a mark of success right there!

Strawberry Compote
Prep time
Cook time
Total time
Recipe type: Dessert
  • 2 pounds Driscoll's strawberries, washed, hulled, and sliced
  • ¼ cup HandCraft Cabernet Sauvignon
  • 1 cup granulated sugar
  • 1 Tablespoon unsalted butter
  • 1 Tablespoon HandCraft Cabernet Sauvignon
  • 1 Tablespoon Cointreau
  • 2 Tablespoons cornstarch
  1. Combine sliced strawberries, ¼ cup Cabernet Sauvignon, and sugar in a 2-quart heavy-bottomed saucepan.
  2. Heat over medium flame so that the berries are barely simmering (you'll probably have to reduce the temperature once they start) until they are softened and liquid reduces, about 25 minutes (low and slow is the best way to go).
  3. Add the butter and stir in until melted (helps with foaming).
  4. In a liquid measuring cup, whisk together the remaining 1 Tablespoon Cabernet Sauvignon, Cointreau, and cornstarch.
  5. Stir into strawberries and cook for 2-3 more minutes, or until thickened.
  6. Cool completely.
You will end up with more than you need. Feel free to use the remaining strawberry filling as a topping for pancakes or ice cream! Store in the refrigerator for up to 3 days.

Vanilla Whoopie Pies
Prep time
Cook time
Total time
Recipe type: Dessert
Serves: 20
  • 2¼ cups all-purpose flour
  • 2 teaspoons baking powder
  • ¾ teaspoon fine sea salt
  • ½ cup (8 Tablespoons) unsalted butter, softened
  • ¾ cup granulated sugar
  • ¼ cup light brown sugar, lightly packed
  • 2 large eggs
  • 2 teaspoons vanilla extract
  • ⅔ cup whole milk
  1. Preheat oven to 375 degrees Fahrenheit. Take out 2 rimmed nonstick baking sheets and set aside.
  2. In a large mixing bowl, whisk together the flour, baking powder, and salt. Set aside.
  3. In the bowl of a stand mixer fitted with the paddle attachment, cream the butter and sugars until light and fluffy, about 3-4 minutes.
  4. Add the eggs, one at a time, fully incorporating the first before adding the second.
  5. Mix in the vanilla extract.
  6. Alternate adding the dry ingredients with the milk in 3 additions, starting with the dry and ending with the milk.
  7. Portion out onto the baking sheets using a #60 (2-teaspoon) cookie scoop.
  8. Bake for 9-10 minutes, or until springy on top on very lightly browned on the edges.
  9. Let sit on baking sheet for 2 minutes, then transfer to wire racks to cool completely.

Whipped Cream
Prep time
Total time
Recipe type: Dessert
  • 1 cup heavy cream
  • 2 Tablespoons confectioner's sugar
  • 1 teaspoon vanilla extract
  • 1 pinch kosher salt
  1. Combine ingredients in a large mixing bowl.
  2. Whip with a hand mixer until light and airy.
  3. Can be made up to 3 hours before needed; just store covered in the refrigerator.

To assemble: Spoon some strawberry compote over the flat side of one whoopie cake/cookie. Top with whipped cream. Apply the flat side of another whoopie cake/cookie to the top and eat immediately.

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  1. Omg yes yes yes! This is so amazing!

  2. This is on the menu for this weekend!!!

  3. Dude, seriously these whoopies are making me drool!

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