These pumpkin whoopie cookies are pretty irresistible. The combination of canned pumpkin and the sweet fall flavors make it a great treat for the season. The cookies themselves are light and fluffy, with a soft texture that will make your mouth water. But it’s the creamy, sweet, and tangy cream cheese filling that really seals the deal, creating a flavor combination that’s hard to beat.

Meet Retro Dessert #2: Whoopie! It’s just so much fun to say. Pennsylvania, Maine, and New Hampshire all claim to be the birthplace of the Whoopie Pie. In Maryland, where I grew up, we refer to them as Gobs. What I remember eating as a child tasted nothing like what you will find in this area of Northern Virginia; there was definitely not a cream cheese frosting sandwiched between the cake-like cookies I grew up with. Instead, the main ingredient for the filling was Crisco. That’s right, beautifully white, glistening, artery-clogging Crisco, which means they were not exactly the healthiest treat, but no one cared so much back then about those kinds of things. These Whoopie Pies are mini-size, and Crisco-free, so you don’t have to feel as guilty while you eat them. They also use pumpkin purée, instead of chocolate; that’s got to be good for you, right? This recipe makes a lot of cookies, so perhaps you should at least eat two or three, seeing as they’re just so darn healthy.

Ingredients:

Whoopie Pies:

• 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 Purée, Chilled
• 2 Eggs, Room Temperature
• 1 Tablespoon Vanilla

Cinnamon Cream Cheese 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 Pies:

1. Heat oven to 350 degrees. Line baking sheets with parchment paper; set aside.
2. In a large bowl, whisk together flour, salt, baking powder, baking soda, cinnamon, and pumpkin pie spice; set aside.
3. In another large bowl, whisk together brown sugar and oil, until well combined.
4. Add the chilled pumpkin purée to the sugar and oil mixture; mix well to combine.
5. Add eggs and vanilla, whisking until well combined.
6. Add flour mixture on top of the pumpkin mixture and whisk until fully incorporated.
7. Using a cookie scoop, drop batter by heaping tablespoons onto prepared baking sheets, at least 1 inch apart.
8. Bake for 15 minutes, or until the cookies are just starting to crack on top.
9. Allow the cookies to completely cool before filling.

Cinnamon Cream Cheese Filling:

1. Cream the butter and cream cheese together for 2 minutes on medium speed.
2. Add the cinnamon and vanilla; mix for 30 seconds on medium speed.
3. Slowly add the powdered sugar, and mix on low speed until well combined.
4. Place the filling into a large resealable plastic bag. Snip the corner off of the bag and pipe the filling onto the bottom side of a cookie. Place another cookie on top of the filling to make a sandwich. Repeat with remaining cookies.

Suggestions:

• Don’t forget to chill your pumpkin purée for at least an hour before starting this recipe.
• If you do not like the taste of pumpkin pie spice, or have none available, increase the amount of cinnamon to 3 tablespoons.
• Use an Open Star Decorating Tip to pipe the filling between your cookies.
• Wrap the whoopie pies in plastic wrap, or make sure they are well covered in plastic. The whoopie pies will stick together if they touch one another.
• Make sure to refrigerate until serving, it makes these much easier to eat. (It also ensures that the cat will not have a huge gob of filling fall on her head.)

Improvements:

• Roll the exposed cream cheese edges of the whoopie pies in miniature chocolate chips or sprinkles.
• Fold finely chopped pecans into the batter.
• CLICK HERE to see all of our past cookie recipes. Make sure to check out the Fall/Autumn/Halloween Cookies section for more great Halloween cookie recipes.

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Pumpkin Whoopie Pie Cookies

Ingredients:

Whoopie Pies:
• 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 Purée, Chilled
• 2 Eggs, Room Temperature
• 1 Tablespoon Vanilla
Cinnamon Cream Cheese 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 Pies:
1. Heat oven to 350 degrees. Line baking sheets with parchment paper; set aside.
2. In a large bowl, whisk together flour, salt, baking powder, baking soda, cinnamon, and pumpkin pie spice; set aside.
3. In another large bowl, whisk together brown sugar and oil, until well combined.
4. Add the chilled pumpkin purée to the sugar and oil mixture; mix well to combine.
5. Add eggs and vanilla, whisking until well combined.
6. Add flour mixture on top of the pumpkin mixture and whisk until fully incorporated.
7. Using a cookie scoop, drop batter by heaping tablespoons onto prepared baking sheets, at least 1 inch apart.
8. Bake for 15 minutes, or until the cookies are just starting to crack on top.
9. Allow the cookies to completely cool before filling.
Cinnamon Cream Cheese Filling:
10. Cream the butter and cream cheese together for 2 minutes on medium speed.
11. Add the cinnamon and vanilla; mix for 30 seconds on medium speed.
12. Slowly add the powdered sugar, and mix on low speed until well combined.
13. Place the filling into a large resealable plastic bag. Snip the corner off of the bag and pipe the filling onto the bottom side of a cookie. Place another cookie on top of the filling to make a sandwich. Repeat with remaining cookies.

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