Borders Line: Be A Badass Baker - Whoopie Pies Three Ways

Learn how to make three kinds of whoopie pies: chocolate peanut butter, pumpkin cream cheese and oatmeal cranberry!

Happy Thanksgiving! You're probably getting really hungry right about now as your house fills up with the savory scents of turkey and stuffing, or TV dinners or pizza - however you choose to spend this fine November day. If you're at work, I hope you have some seriously delicious leftovers in store.

For my family dinner, I made a series of whoopie pies, trying out three different recipes with three successful results. I'm telling my family I made these for them, but in truth, I made them for YOU, dear Badass readers. 

Whoopie Pies Three Ways

Whoopie pies are a traditional New England dessert, so I thought bringing them to my super southern Thanksgiving, with its proliferance of pecan pies, would shake things up a bit. I do not recommend making all three kinds of whoopies at once as I did, because I had to wash and dry my standing mixer bowl SEVEN times that night. Making only one of these recipes would be quite fast and easy - all three made for a bit of a marathon. Still, I had the kitchen to myself and I kept myself entertained, and it was a pretty delightful few hours. 

First things first! Beer and tunes. 

I went with The Beatles' White Album and, naturally, Pumpkinator by Saint Arnold, an imperial pumpkin stout that's extremely limited, extremely flavorful and 10% ABV. This is a wonderful beer, my friends. It's not easy to get your hands on a bottle, so if you do, hold tight and never let go. (Not true. Drink it. Drink it UP.)

For my first recipe, I went with Chocolate Whoopie Pies with a Crunchy Peanut Butter Filling. For the pies I used a modified recipe from the Joy the Baker cookbook, and I used my own peanut butter frosting recipe, first published on this site for my banana bread cupcakes post.

Preheat your oven to 350 degrees F. Line two baking sheets with parchment paper or Silpats. Take your butter out of the fridge! I always forget to take out my butter and then I have to use the microwave to soften it, which is a tricky endeavor. You can also squeeze your butter (in the paper wrapping, obviously, because otherwise gross) in your hands to soften it faster. 

Pro Tip!

Buy Silpats if you have any interest in baking. These reusable, non-stick, oven-safe baking mats will rescue your cookies on the regular.

Chocolate Whoopie Pie Ingredients

2 cups all-purpose flour
1/2 cup unsweetened cocoa powder
1 1/4 teaspoon baking soda
1 teaspoon salt
1 teaspoon instant espresso powder 
1/2 cup unsalted butter, softened
1/2 cup granulated sugar
1/2 cup packed brown sugar
1 large egg
2 teaspoon pure vanilla extract
1 cup buttermilk

In a bowl, whisk together all of your dry ingredients except the sugars: flour, cocoa powder, baking soda, salt and espresso powder. In another bowl, beat together the butter and white and brown sugars for about four minutes, until light and fluffy. 

Pro Tip!

Scrape the sides of your mixing bowl often, in between adding ingredients - OR buy this amazing invention, a mixer attachment that scrapes your bowl for you as it mixes! 

Add your egg and beat for a minute, then beat in the vanilla. 

While the mixer's going, start adding the dry ingredient mixture a little at a time, alternating with a little of the buttermilk at a time, until it's all just barely blended. Finish mixing it yourself with a spatula, because you don't want to over-mix the batter. 

Spoon the batter onto the prepared cookie sheets in rounded scoops, an inch apart from one another. 

Pro Tip!

I know I keep telling you to buy stuff, and you certainly don't have to - you can make almost anything with very basic kitchen accessories. But I'm addicted to buying baking appurtenances, and a few wise purchases really will make your life easier if you bake often. This cookie scoop makes transferring the dough from the bowl to the baking sheet fast and tidy, resulting in cookies that are uniform in shape and size - important for whoopie pies, since you'll be matching the cookies together to make sandwiches. 

Bake 12 to 14 minutes, until you can stick a toothpick into the center of the cookie and it comes out clean, but the cookies are still soft.

Leave them to cool on the pan for a few minutes until they've firmed up a bit, then transfer them to a cooling rack to cool completely. 

Pro Tip!

Don't ever frost a cookie or a cake until it's fully cooled. Ever ever ever!

Crunchy Peanut Butter Filling Ingredients 

1/2 cup unsalted butter, softened 
1 cup creamy peanut butter 
3-6 tablespoons milk (add as needed)
2 cups confectioners’ sugar
1/4 cup chopped, roasted and salted peanuts 

Combine your butter and peanut butter in a mixing bowl and beat with an electric mixer until it’s fully incorporated. Gradually mix in the sugar, and as the frosting starts to get thick, incorporate the milk one tablespoon at a time until it’s a whipped, spreadable mixture. 

Use a spatula to fold in the chopped peanuts. Once your whoopie pies are cooled, start pairing together the cookies that match best in shape, and put a dollop of frosting on one. 

Sandwich that baby!

Next: Oatmeal Whoopie Pies with Cranberry Frosting. I just used a typical oatmeal cookie recipe and made up the cranberry frosting recipe, and they turned out delicious, but they aren't as cute as the others. The cookies are a little flatter than the other whoopie pies - I'd recommend using smaller scoops of the dough than I used, so they won't spread as much. 

Preheat your oven to 375 degrees F. Prepare two baking sheets with silpats or parchment paper. Take your butter out of the fridge to soften!

Oatmeal Whoopie Pie Ingredients

1 cup unsalted butter, softened
1 cup granulated sugar
1 cup packed brown sugar
2 large eggs
1 teaspoon vanilla extract
2 cups all-purpose flour
1 teaspoon baking soda
1 teaspoon salt
1 1/2 teaspoons ground cinnamon
3 cups quick cooking oats

In a bowl, whisk together your flour, baking soda, salt and cinnamon. Cream the butter, white and brown sugars together in your mixer. Beat in the eggs and vanilla gradually. Gradually beat in the flour mixture. Gradually beat in the oats. Cover and chill the dough for an hour. (Eh, that's what you're supposed to do, but I was short on time and didn't chill the dough, and it turned out just fine.)

Spoon the dough in SMALL (smaller than you see here) rounded, evenly sized balls at least an inch apart on your baking sheets and bake for 8 to 10 minutes. Allow the cookies to cool on your baking sheet for a few minutes before transferring to a wire cooling rack to cool completely before frosting them. 

See, too big and flat! But delicious. Totally delicious. 

Cranberry Filling Ingredients

1 cup cranberry sauce
1 teaspoon vanilla extract
1 egg white
1 dash salt
2 teaspoons fresh lemon juice
2 cups confectioners' sugar

Beat together all of the ingredients except the sugar until they're combined, and then gradually add in the sugar. Beat for a really long time, until it peaks (meaning the frosting makes stiff little peaks). If the frosting doesn't seem thick enough for you, add more confectioners' sugar until it's the right consistency. Remember, I made this one up and I added the sugar gradually, so I'm estimating on the amounts.

Pro Tip!

To separate the white of an egg, break your egg at its midpoint over a bowl, holding the two halves upright, and pour the egg from one half of the shell to the other, letting the egg white fall into the bowl but keeping the egg yolk in the shell. It's really easy - the egg does it naturally. Keep doing this until all of the white has fallen into the bowl.

Match your cookies up by shape and size, and put a dollop of frosting on one side. Then sandwich that mother!

And finally, Pumpkin Whoopie Pies with Cream Cheese Filling. I slightly modified Martha Stewart's recipe, but only slightly because, well, it's Martha. Homegirl knows what she's doing. 

You know the drill: preheat your oven to 350 degrees F. Line two baking sheets with silpats or parchment paper. Take your butter out of the fridge to soften.

Pumpkin Whoopie Pie Ingredients

3 cups all-purpose flour
1 teaspoon salt
1 teaspoon baking powder
1 teaspoon baking soda
2 tablespoons ground cinnamon
1 tablespoon ground ginger
1/3 tablespoon ground cloves
1/3 tablespoon ground nutmeg
1/3 tablespoon ground allspice
2 cups packed brown sugar
1 cup vegetable oil
3 cups pumpkin puree, chilled
2 large eggs
1 teaspoon pure vanilla extract

Whisk together all of your dry ingredients except the sugar in a bowl: flour, salt, baking powder, baking salt, all of your spices. Beat together the brown sugar and oil in your mixer until it's incorporated. Mix in the pumpkin puree. Mix in the eggs and vanilla. Then sprinkle in the flour mixture gradually as your mixer is running until it's all fully blended. 

Spoon the batter onto your cookie sheets in small, even, rounded scoops about an inch apart from one another. I actually filled up both cookie sheets and had some batter left, so I sprayed a small loaf pan and poured the rest in there for some pumpkin bread. Bake for about 15 minutes, until tops are just beginning to crack and a toothpick inserted in the middle comes out clean. Let cool for a few minutes on pan before transferring to the wire rack to cool completely before frosting. 

Cream Cheese Filling Ingredients

3 cups confectioners' sugar
1/2 cup unsalted butter, softened
8 ounces cream cheese, softened
1 teaspoon pure vanilla extract

Pro Tip!

This is a standard cream cheese frosting that takes about two minutes to make and is ridiculously tasty. Learn it, love it, live it. Memorize it. Make it constantly. It's terrific for cakes, cookies, just spread on bread and gobbled. 

Sift the sugar into a bowl. (You can just use a fine wire mesh colander if you don't have a sifter.) Beat together your butter and cream cheese until smooth. Add the vanilla and beat. Gradually add the sugar as you mix, beating until just smooth. 

Pair together the cookies by shape and size, and add a dollop of cream cheese frosting to one cookie (crazy Martha suggests using a pastry bag to pipe it on, but that's because she's a tyrannical perfectionist). 

Sandwich that sucker!

And there you have it! Three equally delicious, equally simple whoopie pie recipes. If you're only going to make one, which one should you make? Well, that's up to you. My favorite is the pumpkin cream cheese whoopie pie. My husband's favorite is the oatmeal cranberry. My sister's favorite is the chocolate peanut butter. Each of these recipes turned out just right, so I recommend choosing the flavors that appeal to you most. 

Or be insane and make all three - only be aware that you'll have a lot of cleaning to do afterwards. After you finish with the Beatles' album and your beer, you may want to watch several episodes of Felicity and switch to champagne cocktails. I can't promise the combination made these whoopie pies taste better, but it certainly didn't hurt.

And have a happy Thanksgiving, or a happy random Thursday!