Pumpkin Whoopie Pies with Cream Cheese Frosting

pumpkinwhoopiesAs a kid, we always went to this local pumpkin farm whenever it was open for the season.

It was a family owned farm, but it was pretty obvious it was owned by a family who really didn’t care too much about appearances, nor pumpkins.

The pumpkins to pick from were mildly attractive at best and they charged like $100/pound per pumpkin so my parents never let us get any from there. I didn’t realize that gigantic orange squash that grow from the earth would cost an obscene amount of money to purchase and then mutilate in the name of Halloween.

However crappy the pumpkin farm was, I was always deathly frightened by their ‘Haunted House.’ It was basically a glorified longer-looking shed filled with remotely creepy odds and ends that were brutally scary to a child but were actually really poorly strewn about to an adult. So the morbid weirdo in me begged my parents to walk through it with me and I would jump and shriek at the poorly tossed plastic skeleton bones and clumpy clouds of fake spiderwebs.

Because I was so spooked out over the house, I had these memories that convinced me that this house was truly terrifying. So one year I insisted to my then-boyfriend that this local pumpkin farm had the creepiest haunted house and we had to go.

We get there and eagerly anticipate walking through that same beat-down shed and the ticket lady was looking at us like, ‘seriously?’ but I had these fond memories of being truly terrified of the badass animatronics and decor, so we entered the haunted house.

A vague monster-music soundtrack crackled in the distance and the scariest thing about it was probably that the mixtape on the tape player (!!) they used still worked. The first few feet of it were those light-up lawn decorations that are usually Christmas-time deer but they were tinted with red lights to look like… red deer? They also peppered in some light-up lawn deco ghost to truly delight their guests with fright.

Later on we entered some mummy tomb where a mannequin in the corner was half-assed draped with bandage tape. Shortly following that was a graveyard scene with foam skulls stabbed onto wrought-iron fencing and an animated skeleton-hand-popping-from-the-grave thingie that creaked with desperation when you walked past.

Lastly, you walked through a fog sequence because fog is the international symbol of fright, and then you were greeted with daylight and $80 pumpkins.

Pretty sure I was dying of embarrassment forever and wasn’t allowed to pick out “awesome dates” for awhile after that one.

Anyway. I still love pumpkin patches and have since found some other local ones who don’t charge an arm and a fake-skeleton leg for some lopsided misfit pumpkin. My fond memories of the pumpkin patch was the inspiration for these whoopie pies, and after seeing similar ones on Lizzy’s blog, I was convinced I had to make some!

These couldn’t be easier to make and make for such a great presentation for parties or just because 🙂 Pumpkin Whoopies get dressed up like pumpkins in the patch with a simple Tootsie Roll ‘stem’ and a minty green gummy ‘leaf.’ Easy-peasy!

…and they don’t cost an arm or leg!


5.0 from 2 reviews
Pumpkin Whoopie Pies with Cream Cheese Frosting
Recipe type: Whoopie Pies, Cookies
Prep time: 
Cook time: 
Total time: 
Serves: 15
These adorable whoopie pies are made to look like pumpkins in the patch and taste as good as they look!
  • 1 box pumpkin cake mi (if you cannot find pumpkin mix, use spice cake)
  • 1 cup pumpkin puree
  • ½ cup buttermilk
  • ⅓ cup oil
  • 2 eggs
  • 1 tsp cinnamon
  • 1 pkg (8 oz) cream cheese, room temperature
  • ¼ cup butter, softened to room temperature
  • 1 tsp vanilla extract
  • 3-4 cups powdered sugar
  • About 15 Tootsie Rolls
  • About 8 Mint Gummy Leaves (if you can't find these (usually in a package with the orange gummies), you may substitute green AirHeads shaped like leaves
  1. Preheat oven to 350 degrees F. Line 2 baking sheets with silicone liners and set aside. Meanwhile, in a large bowl, combine the cake mix, buttermilk, pumpkin, oil, cinnamon and eggs with a rubber spatula until blended.
  2. Scoop ¼ cup-sized balls of dough and place them 1-2" apart on the prepared baking sheets. Bake for approx. 15 minutes, rotating pans halfway through baking time, until whoopie pies look set and spring back lightly when touched. Cool for about 10 minutes on the pan, then transfer to a wire rack. Cool completely.
  3. In the bowl of a stand mixer, beat together the cream cheese, butter and vanilla with the paddle attachment until creamy. Gradually add in the powdered sugar, about 1 cup at a time, until frosting is light and fluffy.
  4. Spoon frosting into a disposable piping bag attached with a large open circle tip (I like Atecco 807) and pipe the frosting high onto the flat side of a whoopie. Top with another like-sized whoopie. Repeat with remaining cookies.
  5. Very gently press a Tootsie Roll into the top of each whoopie pie to create a stem, then attach a half of a green mint leaf to the whoopie pie with a little frosting. Serve immediately!

DSC_0512ANothing beats the classic combination of luscious, light cream cheese frosting and soft and perfectly spiced pumpkin whoopies! I have a feeling you’ll agree! 🙂

Have a fantastic day!!

xo, Hayley

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  1. bahahahaa omg. Best date ever 😛 I used to go to like haunted garages or haunted hay rides. All I remember being pretty impressive, but I wonder how they’d seem now?

    Regardless these whoopie pies are so creative and cute and look pumpkin-licious!

  2. Shut the front door! These are so damn adorbs!

  3. These are seriously adorable. LOVE LOVE LOVE. And pumpkin patches with their ridiculously expensive pumpkins…what is that about? I love farmers markets and fresh produce, but pumpkins? I’ll go to the grocery store, thank you.

  4. These are adorable! I’d much rather go through that crappy haunted house than the really scary ones, I’m a big wuss!

  5. These are just the cutest! Pinned!

  6. I love how you made these into actual pumpkins. So adorable!

  7. Tonette Joyce says:

    So darned cute!

  8. These are so cute!! I love it!

  9. These seriously are the most adorable fall cookies I have seen! You are so creative. I’m pinning this now! Thanks for the great recipe.

  10. Bahahaha that sounds like an AWESOME date. What a great story you got out of it! I had a similar experience when I dragged my husband and his family to the Winchester Mystery House – I SWORE as a kid it was the coolest thing ever. As an adult? Meh. These pumpkin whoopie pies are too cute for words!

  11. So if you follow the directions you have 1/2 cup of buttermilk left over. Why include it in the ingredients list?

    • thedomesticrebel says:

      Mickey, I forgot to add it into the instructions – the buttermilk goes into the pumpkin whoopie pie batter. Thanks for bringing it to my attention!

  12. Why do you say to serve immediately?


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