Step 1 of 14
One-Bowl Gingerbread Whoopie Pies
Place the oil, brown sugar, vanilla, and molasses in large mixing bowl and whisk to combine.
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Step 2 of 14
One-Bowl Gingerbread Whoopie Pies
Add the eggs and yolk one at a time, whisking after each. Add the buttermilk and whisk until well combined.
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Step 3 of 14
One-Bowl Gingerbread Whoopie Pies
Put a sheet of parchment paper or a plate on a work surface and sift the flour, baking powder, baking soda, salt, and spices onto it. Add dry ingredients to the bowl in three additions, folding them together until well blended.
PRO TIP If you have it, parchment paper is a handy tool for one-bowl baking; you can use it not only for lining a pan, but also to use as a landing pad when sifting dry ingredients.
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Step 4 of 14
One-Bowl Gingerbread Whoopie Pies
Cover the bowl and freeze until batter is scoopable (it will hold a soft shape on a spoon), about 1 hour.
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Step 5 of 14
One-Bowl Gingerbread Whoopie Pies
Preheat the oven to 350°F.
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Step 6 of 14
One-Bowl Gingerbread Whoopie Pies
Line a baking sheet with parchment paper or grease with butter.
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Step 7 of 14
One-Bowl Gingerbread Whoopie Pies
Scoop or measure 15 portions of dough onto the prepared baking sheet, using about 1 1/2 tablespoons for each, and spacing them evenly apart. Return any remaining batter to the freezer.
PRO TIP Scrape bowl well, as you will be reusing it to make the frosting. Wipe with a paper towel, if necessary.
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Step 8 of 14
One-Bowl Gingerbread Whoopie Pies
Bake the whoopie pies on middle rack of oven for 5 minutes. Rotate pan and continue baking until whoopie pies are dry and the center bounces back when gently pressed, 8-10 minutes.
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Step 9 of 14
One-Bowl Gingerbread Whoopie Pies
Check to see that whoopie pies are done. Remove from oven or add time as needed. Transfer whoopie pies to cooling racks. Repeat the scooping and baking steps with the remaining batter. When done, let the whoopie pies cool completely.
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Step 10 of 14
One-Bowl Gingerbread Whoopie Pies
Place the butter, cream cheese, and vanilla in the large mixing bowl. Beat on medium speed until smooth, scraping down the sides of the bowl as needed.
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Step 11 of 14
One-Bowl Gingerbread Whoopie Pies
Put a sheet of parchment or a plate on a work surface and sift the powdered sugar, salt, and cinnamon onto it. Add dry ingredients to cream cheese mixture a little at a time, mixing on low speed to incorporate between each addition.
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Step 12 of 14
One-Bowl Gingerbread Whoopie Pies
Increase speed to medium to medium-high, and beat mixture until smooth.
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Step 13 of 14
One-Bowl Gingerbread Whoopie Pies
Flip half of the cooled whoopie pies flat-side up. Scoop about 2 tablespoons of filling onto each flat side, then press a rounded-side-up whoopie pie on top until the filling comes out to the edges. Or, generously spread flat filling on whoopie pies to edges using a small offset spatula or butter knife, smoothing edges if desired, then top each with a rounded-side-up whoopie pie.
PRO TIP If you want the edges of the filling that pokes out between the cookies to be smooth, use a cookie scoop to measure the filling and place it in the center of the pie. Then press down lightly with the other pie. If you don't have a cookie scoop, try smoothing the edges of the filling with a small offset spatula or butter knife.
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Step 14 of 14
One-Bowl Gingerbread Whoopie Pies
Serve the whoopie pies immediately, or refrigerate for one hour and serve cold. Wrap leftover pies in waxed paper or plastic wrap and refrigerate in a container for up to three days, or freeze for up to one month.