Pumpkin Whoopie Pies with Dulce De Leche Filling

I have a collection of these cookie scoops now that I use to ensure even-size muffins, cookies, and in this case, whoopie pies. It’s definitely one of my must-have kitchen tools. The non-stick muffin tin was perfect for this recipe because I didn’t have to use paper liners to prevent the whoopie pies from sticking to the tin, and the micro-textured pattern ensures even baking – meaning all my whoopie pies were evenly baked at the same time. Whoopie!

Now, given this was my first foray into making whoopie (pies) I definitely had some lessons learned for next time. I overfilled the muffin tins  a bit too high, so the cookies came out a little more like muffins than intended. You can also bake these on a cookie sheet instead of the muffin tin, but this muffin tin method keeps them from spreading too much.

Next time I’ll just have to use two tins and fill them halfway. So some of the whoopie pies came out looking like a muffin filled with creamy fluff, like the photo below, but looks don’t matter in the baking world – these still tasted amazing. The only change I made to the recipe for the whoopie pies was instead of using cardamom (since I didn’t have it on hand) I swapped in nutmeg, a favorite fall spice of mine. And after one bite of these my loyal taste testing sister-in-law said that these “taste like Christmas.” Translation: two thumbs way up!

The dulce de leche filling adds an amazing flavor that compliments the pumpkin and cranberry cookie. I was not able to find canned dulce de leche in my grocery store, so we made our own over a double boiler on the stove using a can of sweetened condensed milk. That was the most time consuming part of this recipe to just continually whisk the condensed milk until it caramelized a bit and turned into dulce de leche, but the amazing flavor was definitely worth the wait!  Mixed with marshmallow fluff and powdered sugar, my only regret about the sweet filling was that I didn’t make more of it. I would recommend doubling the filling recipe so that you can be extra generous when making these whoopie pies.

For a first attempt at whoopie pies, I’d have to consider this recipe a huge success. The pies didn’t last long at all at the house, and kept well in the fridge for the two days that they lasted, though I do recommend eating them the same day you bake them to really enjoy the best flavor. So if you’re looking to up the ante on your pumpkin spice baking this fall, definitely whip up at batch of these Pumpkin Whoopie Pies with Dulce De Leche Filling for a good cause!

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Pumpkin Whoopie Pies with Dulce De Leche Filling

Yield: 16 Whoopie Pies

Prep Time: 1 Hour

Cook Time: 12 Minutes

Total Time: 1 Hour 12 Minutes

Recipe from Dorie’s Cookies by Dorie Greenspan

Ingredients:

For the whoopie pies

• 1 3/4 cups all-purpose flour
• 3/4 teaspoon ground cinnamon
• 1/2 teaspoon ground cardamom (or substitute Nutmeg if you don't have cardamom)
• 1/2 teaspoon baking powder
• 1/2 teaspoon baking soda
• 1 stick (8 tablespoons) unsalted butter, cut into chunks
• 3/4 cup sugar
• 1/2 teaspoon fine sea salt
• 1 large egg 
• 1 1/2 teaspoons pure vanilla extract
• 1/2 cup pumpkin puree (not pumpkin pie filling)
• 1/2 cup buttermilk
• 3/4 cup fresh cranberries (dried cranberries can be substituted)

For the filling

• 1 stick (8 tablespoons) unsalted butter, cut into chunks
• 1 cup marshmallow crème (or Marshmallow Fluff)
• 1/4 cup confectioners’ sugar
• Pinch of fine sea salt
• 1/4 cup dulce de leche, homemade or store-bought 

Directions:

1. Position the racks to divide the oven into thirds and preheat it to 375 degrees F. Butter or spray two standard muffin tins (do this even if the tins are nonstick).
2. To make the cookies: Whisk the flour, cinnamon, cardamom, baking powder and baking soda together.
3. In a large bowl with a hand mixer, beat the butter, sugar and salt together on medium speed until smooth, about 2 minutes. Add the egg and beat for another 2 minutes or so, until creamy. Beat in the vanilla. Reduce the mixer speed to low, add the pumpkin puree and beat until it’s fully incorporated; don’t be discouraged when the mixture curdles — it will soon smooth out.
4. Turn off the mixer, scrape down the bowl and add half of the dry ingredients. Pulse to begin the mixing and then mix on low, scraping the bowl as needed, until the flour mixture is blended in. Beat in the buttermilk. Turn off the mixer, add the remaining dry ingredients, pulse and then mix on low until you have a lovely smooth batter. Switch to a flexible spatula and fold in the cranberries. Don’t be too thorough — it’s better to have an uneven mix than to break the berries and turn the batter red.
5. Using a medium cookie scoop, scoop out level portions of dough and fill the muffin tins. The scoops of dough will sit upright in the center of the tins, but when baked they’ll melt evenly into the cups.
6. Bake the whoopie pies for 11 to 12 minutes, rotating the pans top to bottom and front to back after 6 minutes, or until they are puffed, golden brown and springy to the touch.
7. Transfer the pan to a rack and let the cookies rest for 5 minutes, then turn them out on the racks and allow them to cool completely.
8. To make the filling: In a medium bowl with a hand mixer, beat the butter, marshmallow crème, sugar and salt together on medium-high speed, scraping the bowl and beater(s) as needed, for about 3 minutes, until very smooth. Lower the mixer speed, add the dulce de leche and beat until thoroughly blended.
9. Using a cookie scoop, place the filling on the flat sides of half of the cookies; sandwich with the other cookies, flat sides down. The cookies can be eaten now, but the filling benefits from a 30-minute stay in the refrigerator. Just don’t eat them from the fridge — you’ll deprive yourself of the cookies’ wonderful texture.

Playing Around

• Whopper-Size Whoopie Pies. If you use a large cookie scoop (one with a capacity of 3 tablespoons) to portion out the dough, you can make 6 really big pies (12 cookies; 6 pies). These bake best when you use an insulated baking sheet or stack two sheets one on top of the other. Line the (top) sheet with parchment paper or a silicone baking mat and bake the cookies for 15 to 17 minutes.

Storing

• The unfilled cookies can be kept covered at room temperature for up to 1 day. Once filled, they can be kept covered in the refrigerator for a day or two, but they’re really best the day they’re made.