Pumpkin Whoopie Pie Cookies

Whoopie Pie Poem

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 tastes 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 kind 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 puree, 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.

Pumpkin Whoopie Pie Cookies


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 Puree, 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


  1. Heat oven to 350 degrees.
  2. Line baking sheets with parchment paper.
  3. In a large bowl, whisk together flour, salt, baking powder, baking soda, cinnamon, and pumpkin pie spice; set aside.
  4. In another large bowl, whisk together brown sugar and oil, until well combined.
  5. Add the chilled pumpkin puree to the sugar and oil mixture, mix well.
  6. Add eggs and vanilla, whisking until well combined.
  7. Add flour mixture on top of the pumpkin mixture, whisk until fully incorporated.
  8. Using a cookie scoop, drop batter by heaping tablespoons onto prepared baking sheets, at least 1-inch apart.
  9. Bake 15 minutes, or until cookies are just starting to crack on top.
  10. Allow cookies to completely cool before filling.
  11. Cream butter and cream cheese together for 2 minutes.
  12. Add cinnamon and vanilla, mix for 30 seconds.
  13. Slowly add powdered sugar, and mix until well combined.
  14. Place filling into a Ziploc bag with the end snipped off.  Pipe filling onto the bottom of one cookie, and then place another on top to make a sandwich.


  • Don’t forget to chill your pumpkin puree 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 4 tablespoons.
  • Use an Open Star Decorating Tip to pipe the filling between your cookies.
  • Wrap 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.)


  • Roll the exposed cream cheese edges of the whoopie pies in mini chocolate chips or sprinkles.
Pumpkin Whoopie Pies

Pumpkin Whoopie Pies


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  • Theresa Tellado

    On Oct 4, 2013 8:42 AM, “Faith, Hope, Love, & Luck Survive Despite a

  • so glad you tried them!! 🙂