Prize-Winning Pumpkin Whoopie Cookies

This is not an Eggland’s Best sponsored post. I did, however, win three free months’ worth of Eggland’s Best egg coupons for sharing this recipe with them. All thoughts, ideas, recipes, pictures, and general silliness contained within this post are solely my own and not necessarily that of Eggland’s Best.

Prize-Winning Pumpkin Whoopie Cookies - These prize-winning whoopie cookies will totally blow your socks off. They're made using pumpkin and chocolate, which is the perfect autumn flavor combination. And, with a cream cheese filling sandwiched in between two of the pumpkin and chocolate-flavored cookies, this is a fall treat you'll simply find hard to resist.

These prize-winning whoopie cookies will totally blow your socks off. They’re made using pumpkin and chocolate, which is the perfect autumn flavor combination. And, with a cream cheese filling sandwiched in between two of the pumpkin and chocolate-flavored cookies, this is a fall treat you’ll simply find hard to resist.

Two years ago, I made these Pumpkin Chocolate Whoopie Cookies and took pictures of them with one of our outdoor Halloween skeletons. Now, you may think that’s a bit odd, but if you knew how big Halloween is around our house, you would know that it’s really rather normal. Anyway, shortly after posting the recipe on Faith, Hope, Love, & Luck, I entered it into Eggland’s Best Spooky Halloween Recipe Contest. And guess what? I actually won. As a reward, they sent me coupons for three month’s worth of free Eggland’s Best eggs.

After winning the contest, I also received a request from them asking if I had any pictures of the Pumpkin Chocolate Whoopie Cookies that didn’t include a skeleton. Guess what? I didn’t. So, I made yet another batch of the whoopie cookies, so I could send them a few pictures without the skeleton. I also included a few pics of some Eggland’s Best eggs in the pictures while I was at it. After all, they’re a company I simply love and have no problem recommending to just about anyone who will listen to me ramble on.

Now, forward to two years later. While looking through some old Halloween recipes, I realized that I never got around to sharing the new non-skeleton pictures with all of y’all. I’m sure it probably had something to do with me getting too busy during the holiday season, putting it off, and then realizing that sharing pictures of Pumpkin Chocolate Whoopie Cookies around St. Patrick’s Day wasn’t exactly the wisest decision. So, since it’s fall, Halloween, and pumpkin is in season, I’m finally sharing the new non-skeleton pictures and recipe with all of y’all today. Enjoy.

Prize-Winning Pumpkin Whoopie Cookies - These prize-winning whoopie cookies will totally blow your socks off. They're made using pumpkin and chocolate, which is the perfect autumn flavor combination. And, with a cream cheese filling sandwiched in between two of the pumpkin and chocolate-flavored cookies, this is a fall treat you'll simply find hard to resist.

Ingredients:

Whoopie Cookies:

  • 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

Filling:

  • 1/2 Cup Unsalted Butter, Softened
  • 1 (8-oz.) Package Cream Cheese, Softened
  • 1 Teaspoon Vanilla
  • 1/2 Teaspoon Cinnamon
  • 3 Cups Powdered Sugar

Prize-Winning Pumpkin Whoopie Cookies - These prize-winning whoopie cookies will totally blow your socks off. They're made using pumpkin and chocolate, which is the perfect autumn flavor combination. And, with a cream cheese filling sandwiched in between two of the pumpkin and chocolate-flavored cookies, this is a fall treat you'll simply find hard to resist.

Directions:

Whoopie Cookies:

  1. Heat oven to 350 degrees. Line a baking sheet with parchment paper or a Silpat mat; set aside.
  2. In a large bowl, whisk together the flour, salt, baking powder, baking soda, cinnamon, and pumpkin pie spice; set aside.
  3. In another large bowl, whisk together the brown sugar and oil; mix well.
  4. Add the chilled pumpkin puree to the sugar and oil mixture; mix well.
  5. Add the eggs and vanilla; mix well
  6. Add the flour mixture to the pumpkin mixture; mix until fully incorporated.
  7. Fold the chopped chocolate into the batter.
  8. 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.
  9. Bake for 12 to 15 minutes, or until the cookies are set and just starting to turn golden brown on their bottoms. Carefully transfer the cookies to a baking rack to cool completely before filling.

Filling:

  1. Cream the butter and cream cheese together for 2 minutes.
  2. Add the cinnamon and vanilla; mix for 30 seconds.
  3. Slowly add the powdered sugar; mix until fully incorporated.
  4. 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.

Prize-Winning Pumpkin Whoopie Cookies - These prize-winning whoopie cookies will totally blow your socks off. They're made using pumpkin and chocolate, which is the perfect autumn flavor combination. And, with a cream cheese filling sandwiched in between two of the pumpkin and chocolate-flavored cookies, this is a fall treat you'll simply find hard to resist.

Suggestions:

  • 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.

Prize-Winning Pumpkin Whoopie Cookies - These prize-winning whoopie cookies will totally blow your socks off. They're made using pumpkin and chocolate, which is the perfect autumn flavor combination. And, with a cream cheese filling sandwiched in between two of the pumpkin and chocolate-flavored cookies, this is a fall treat you'll simply find hard to resist.

Improvements:

  • 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.
  • CLICK HERE to see the original recipe post for Pumpkin Chocolate Whoopie Cookies.

Prize-Winning Pumpkin Whoopie Cookies

Prize-Winning Pumpkin Whoopie Cookies

Ingredients:

    Whoopie Cookies:
  • 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
  • Filling:
  • 1/2 Cup Unsalted Butter, Softened
  • 1 (8-oz.) Package Cream Cheese, Softened
  • 1 Teaspoon Vanilla
  • 1/2 Teaspoon Cinnamon
  • 3 Cups Powdered Sugar

Directions:

    Whoopie Cookies:
  1. Heat oven to 350 degrees. Line a baking sheet with parchment paper or a Silpat mat; set aside.
  2. In a large bowl, whisk together the flour, salt, baking powder, baking soda, cinnamon, and pumpkin pie spice; set aside.
  3. In another large bowl, whisk together the brown sugar and oil; mix well.
  4. Add the chilled pumpkin puree to the sugar and oil mixture; mix well.
  5. Add the eggs and vanilla; mix well
  6. Add the flour mixture to the pumpkin mixture; mix until fully incorporated.
  7. Fold the chopped chocolate into the batter.
  8. 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.
  9. Bake for 12 to 15 minutes, or until the cookies are set and just starting to turn golden brown on their bottoms. Carefully transfer the cookies to a baking rack to cool completely before filling.
  10. Filling:
  11. Cream the butter and cream cheese together for 2 minutes.
  12. Add the cinnamon and vanilla; mix for 30 seconds.
  13. Slowly add the powdered sugar; mix until fully incorporated.
  14. 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.
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Prize-Winning Pumpkin Whoopie Cookies - These prize-winning whoopie cookies will totally blow your socks off. They're made using pumpkin and chocolate, which is the perfect autumn flavor combination. And, with a cream cheese filling sandwiched in between two of the pumpkin and chocolate-flavored cookies, this is a fall treat you'll simply find hard to resist.

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MORE GREAT PUMPKIN RECIPES

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Cinnamon Pumpkin Snaps

Pumpkin Streusel Breakfast Squares

Canned pumpkin is a quick and easy way to add flavor and moisture to your favorite baked goods and sweets. Not just for pies, pumpkin puree can be used to make all kinds of delicious treats, including fudge. From cookies and bread to whoopie pies and muffins, canned pumpkin purée is an easy way to add delicious fall flavor to your favorite recipes. CLICK HERE for the recipes.