chocolate pumpkin whoopie pies

I have a confession to make... every time I've made whoopie pies, I've had a disaster. The first time I tried, they came out hard and thin like sugar cookies. The second time, they weren't bad, but they were huge. Like, GIANT! I had definitely underestimated how much they would spread. And the filling came out gross. I guess third time's the charm! I made these sweet little pumpkin whoopie pies with chocolate filling and they were perfect. I watched in the oven as they didn't spread out obscenely, and I was beyond happy when my filling was fluffy and delicious and not watery or lumpy. Ahhh, much better. Not to mention, they're so cute!

Like little bites of autumnal deliciousness. Also, I am quite happy that they came out looking exactly like the picture of the originals. If you've ever baked from a cookbook or magazine and you see the pictures, you know that 90% of the time, your food looks NOTHING like the picture... so I was happily surprised! We made this today in my first Baking Class and they came out just as good as they did when I tested the recipe a couple of days ago. Thank goodness... you know how it usually is, when you make food with/for someone else, it doesn't come out right. The planets must have been aligned in my favor today! She took some whoopies with her, and she emailed me shortly after she got home, saying "My family loves them!" Music to my ears. These are really yummy and really easy, and if the whoopie-ly challenged (such as myself) can make them, so can you! P.S. do you prefer your whoopie pies with a powdered sugar coat (like above) or simply naked (like below)? Not judging you if you say you like naked whoopies... I'll just laugh. A lot. 🙂

{Adapted from Everyday Food, November 2011}

Print Recipe

chocolate pumpkin whoopie pies

Prep Time20 minutes mins

Cook Time12 minutes mins

Total Time32 minutes mins

Course: Cookies

Servings: 20

Author: Valentina | The Baking Fairy

Ingredients

• *for the cookies*
• 2 cups all-purpose flour spooned and leveled
• 2 teaspoon pumpkin pie spice
• 1 ½ teaspoon baking powder
• ¼ teaspoon salt
• 2 eggs
• ¾ cup pumpkin puree NOT pumpkin pie mix!
• 1 cup light brown sugar packed
• ⅓ cup unsalted butter melted
• ¼ cup heavy cream
• *for the chocolate filling*
• ¼ cup unsalted butter at room temperature
• ½ cup heavy cream
• ⅔ cup unsweetened cocoa powder
• 1 ¾ cups powdered sugar plus more for serving

Instructions

• Preheat the oven to 350F.
• In a medium bowl, whisk together flour, pumpkin pie spice, baking powder, and salt.
• In a large bowl, whisk together eggs, pumpkin puree, brown sugar, melted butter, and ¼ cup heavy cream. Add flour mixture to egg mixture and whisk until combined.
• Drop dough in 1 tablespoon-sized mounds (or use a cookie scoop), onto a parchment or silicone lined baking sheet. Aim for 12 per sheet! Bake until tops of cookies spring back when gently pressed, 10-12 minutes. Rotate sheets halfway through. Transfer to wire racks to let cool completely.
• In a medium bowl, using an electric mixer, beat the room temperature butter for the filling until whipped and creamy. Add in the cream, cocoa powder, and powdered sugar, and beat on medium high until fluffy, about 2 minutes. Scrape the bottom and sides often if using a stand mixer.
• Scoop filling into a large Ziploc bag, cut a small hole in a corner, and pipe on the underside of half the cookies, then top with remaining cookies. When ready to serve, dust with additional powdered sugar. Enjoy!