“If You Give a Skeleton a Pumpkin Chocolate Whoopie Cookie.” That sounds so much more exciting than, “If You Give a Mouse a Cookie,” right? I think so. So why am I posing one our outside skeleton friends with cookies you might ask? Well, that’s what happens when all of your Halloween party guests devour almost all of your baked goods and you realize that you forgot to photograph them for your #Choctoberfest recipe post. It happens. Well, it does in my life anyway. So, do you find yourself wondering just what would happen if you gave a skeleton a cookie? Well, that skeleton would most likely drop it on the ground; their jaws aren’t so great at holding things like cookies, no matter how yummy they might be. So just ignore that little bit of dirt you see there on that one lonely ol’ whoopie cookie. It’s there for a reason.
I first made these cookies over three years ago for a retro-themed bachelorette party a friend was hosting, and was shocked at how many cookies the recipe made. There were only about six guests at that bachelorette party, so these cookies went a long way. However, when making these cookies for a large party, I suddenly realized that they didn’t make quite as many as I thought they would. When all was said and done, and all of the rejects were gobbled up to hide the evidence of their existence, this recipe yielded about twenty-four whoopie cookies. That’s about normal for most cookie recipes, but large parties definitely require more cookies. Or at least they do if you plan on having leftovers to take pictures of or hand out to your neighborhood ghouls and goblins. Make a double batch if that’s the case, and don’t forget to give one to your favorite skeleton. He’ll most likely drop it on the ground, but that’s not his fault. Being a skeleton sucks.
- 3 Cups All-Purpose Flour
- 1 Teaspoon Kosher Salt
- 1 Teaspoon Baking Powder
- 1 Teaspoon Baking Soda
- 2 Tablespoons Ground Cinnamon
- 2 Tablespoons Pumpkin Pie Spice
- 2 Cups Light Brown Sugar, Packed
- 1 Cup Canola Oil
- 3 Cups Pumpkin Puree, Chilled
- 2 Eggs, Room Temperature
- 1 Tablespoon Vanilla
- 1 (3.5-oz.) Milk Chocolate Bar, Finely Chopped
- 1 (3.5-oz.) Dark Chocolate Bar, Finely Chopped
- 1/2 Cup Unsalted Butter, Softened
- 1 (8-oz.) Package Cream Cheese, Softened
- 1 Teaspoon Vanilla
- 1/2 Teaspoon Cinnamon
- 3 Cups Powdered Sugar
- Heat oven to 350 degrees.
- Line a baking sheet with parchment paper or a Silpat mat.
- In a large bowl, whisk together the flour, salt, baking powder, baking soda, cinnamon, and pumpkin pie spice; set aside.
- In another large bowl, whisk together the brown sugar and oil; mix well.
- Add the chilled pumpkin puree to the sugar and oil mixture; mix well.
- Add the eggs and vanilla; mix well
- Add the flour mixture to the pumpkin mixture; mix until fully incorporated.
- Fold the chopped chocolate into the batter.
- Using a cookie scoop, drop the batter by heaping tablespoons onto the prepared baking sheet, making sure to leave them at least 1-inch apart.
- Bake 12 to 15 minutes, or until the cookies are set and just starting to turn golden brown on their bottoms.
- Carefully remove the cookies to a baking rack to cool completely before filling.
- Cream the butter and cream cheese together for 2 minutes.
- Add the cinnamon and vanilla; mix for 30 seconds.
- Slowly add the powdered sugar; mix until fully incorporated.
- Place the filling into a large Ziploc bag, snip off the corner, and then pipe the filling onto the bottom of one cookie. Place another cookie on top of the filling to make a sandwich. Repeat with the remaining cookies.
- Don’t forget to chill your pumpkin puree for at least two hours. The chilled pumpkin ensures that the whoopie cookies will not spread when baking.
- Use an Open Star Decorating Tip to pipe the filling between the cookies.
- If using a piping bag, split the filling into two batches; it will be much easier to work with.
- Store the cookies in an airtight container with a piece of plastic wrap between each layer. The whoopie pies will stick together if they touch one another.
- Make sure to refrigerate the cookies due to the cream cheese. Refrigerating the cookies also makes them easier to eat.
- Roll the exposed cream cheese edges of the whoopie pies in mini chocolate chips or sprinkles.
- If you do not like the taste of pumpkin pie spice or have none available, increase the amount of cinnamon to 4 tablespoons.
- Individually wrap each whoopie cookie to give as a gift.
Don’t forget to enter the #Choctoberfest Rafflecopter Giveaway above for your chance to win a sweet prize pack.
I’ll be joining the Fiesta Friday Link Party today. Head on over HERE to see what everyone else is bringing to the celebration.
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