Pumpkin Whoopie Pies with a Whipped Cinnamon Filling

Brace yourselves for bites of heaven — these pumpkin whoopie pies with whipped cinnamon filling are the perfectly sweet and soft, cream-filled cookie sandwiches you need this fall… and probably year-round, too.

If you’re a fan of pumpkin-flavored sweet treats, I’ve got a full list of yummy confections you MUST try. Simply type “pumpkin” into the search bar of blessthismessplease.com, but to get you started, here are a few of my favorites: Cake Mix Pumpkin Chocolate Chip Cookies, Perfect Pumpkin Bread, and Extra Thick Pumpkin Cake. Yum yum!

Pumpkin Whoopie Pies with a Whipped Cinnamon Filling

I’m not sure there’s a better sweet treat than whoopie pies. The soft bites of fluffy cookie, the creamy frosting middle, the cute sandwich look of them?! They are truly a favorite of mine, and add pumpkin and cinnamon flavors to the mix, and I am in straight-up heaven.

They also look a lot more decadent and fancy to make than they really are. For real, all you need is a hand or stand mixer and an approachable list of ingredients (many of which you probably already have in your baking cabinet). They come together so quickly and easily, and they’re a joy for both kids and adults to devour after dinner, or before — you can trust me on that!

My husband isn’t a huge cinnamon fan, so he actually prefers these cookies solo without the filling, and they are great that way, too. (And the perfect milk dunker.) However you take them, these are sure to bring a whole lot of sweet memories to your home this fall!

Why do they call it a whoopie pie?

Based on Amish legend, whoopie pies were made from leftover cake batter and were considered a special treat for little ones in the Amish community because, when they’d find them in their lunches, they’d cry, “Whoopie!”

How do you make a whoopie pie?

Using an electric mixer, combine the batter ingredients, and scoop the batter onto a parchment-lined baking sheet with a one-ounce scoop spaced two inches apart. Bake them at 350 degrees F. for 10 to 12 minutes, until the tops spring back when you press on them.

Beat together the filling ingredients with an electric mixer until well combined, about 5 minutes. Allow the cookies to cool, and then spread about a tablespoon of filling onto the flat side of one cookie before topping it with the flat side of another cookie. Voila! Or should I say, “Whoopie!”

Do whoopie pies need to be refrigerated?

Once whoopie pies are prepped, you can store them in an airtight container in the fridge. Allow them to warm to room temperature on a plate for about 5 minutes before serving.

How do you keep whoopie pies from sticking?

The butter in the batter, plus the parchment paper they bake on, should keep your whoopie pies from sticking. If you experience stuck cookies to the parchment paper, you could also spray the parchment paper lightly with canola oil cooking spray.

 

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Pumpkin Whoopie Pies with a Whipped Cinnamon Filling


  • Author: Melissa Griffiths - Bless this Mess
  • Prep Time: 15 min
  • Cook Time: 8 min
  • Total Time: 1.5 hours
  • Yield: 2 dozen sandwich cookies 1x

Description

Brace yourselves for bites of heaven — these pumpkin whoopie pies with whipped cinnamon filling are the perfectly sweet and soft, cream-filled cookie sandwiches you need this fall… and probably year-round, too.


Scale

Ingredients

For the cookies:
  • 1/2 cup butter, softened
  • 1 1/4 cups granulated sugar
  • 2 eggs, at room temperature
  • 1 cup pumpkin puree
  • 1 teaspoon vanilla extract
  • 2 cups flour
  • 1 teaspoon baking powder
  • 1 teaspoon baking soda
  • 1 teaspoon ground cinnamon
  • 1/2 teaspoon salt
For the filling:
  • 1/2 cup salted butter, softened
  • 1/3 cup whipping cream, at room temperature
  • 1/2 teaspoon cinnamon
  • 1 teaspoon vanilla bean extract (or 1 teaspoon vanilla extract)
  • 2 1/2 to 3 cups powdered sugar

Instructions

  1. Preheat the oven to 350 degrees F.
  2. In a large bowl, or the bowl of your stand mixer with the cookie paddle attached, beat the butter and sugar on medium speed until light in color and fluffy, about 3 minutes.
  3. Add the eggs, and mix to incorporate.
  4. Add the pumpkin and vanilla, and mix to combine.
  5. Sprinkle the flour over the top of the butter mixture, and then sprinkle the baking powder, soda, cinnamon, and salt over the flour. Mix until well incorporated, about a minute.
  6. Using a one-ounce scoop, scoop the batter onto a parchment lined baking sheet, spacing them 2 inches apart.
  7. Bake for 10 to 12 minutes, until the cookie springs back slightly when touched.
  8. For the filling: Use a stand mixer or electric hand mixer to beat the butter, whipping cream, cinnamon, and vanilla bean extract with the wire whisk attachment. Beat at medium-high speed until very light and fluffy, about 5 minutes.
  9. Add the powdered sugar, and beat for another 3 to 5 minutes. The filling will be very fluffy and a medium-thin consistency. If the icing is too thick, add a touch of cream and beat again. If it is too thin, add a little more powdered sugar and beat again.
  10. When the cookies have cooled, spread a tablespoon of filling onto flat side of one cookie; top with flat side of second cookie to make a sandwich. Repeat with remaining cookies and filling.
  11. Store in covered container.

Notes

  • Using a scoop for the cookie dough makes the cookies nice and round. If you don’t have a scoop, just take a little time and use two spoons to transfer the dough to the baking sheet. The more uniform the scoops of dough, the prettier your cookies will be.
  • The cookies are delicious without the filling, too. My husband, who is not a cinnamon fan, liked the cookies plain and so did my kids.
  • Category: dessert
  • Method: bake
  • Cuisine: American

Keywords: whoopie pie, pumpkin pie, pumpkin cookie, cookie recipe, pumpkin dessert, dessert

This post was originally published in 2012, and has been updated and rephotographed in September 2019.

Pumpkin whoopie pies with cinnamon filling are deliciously sweet and wickedly adorable cookie sandwiches that are easy-to-make desserts to ring in autumn.

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38 Recipes for Busy Moms
17 Responses
  1. solarpoweredyogi.com

    Gurrrrrrrrl, I am feeling you with the blogging funk. I have literally thousands of photos to sort and process and a million things to write about, but I’m just like, no, it’s baking and reading in pajamas time.

  2. Jess from Coxs Corner

    Oh man, these look amazing! I love whoopie pies! I’m sorry you’re in a funk…I never got that vibe off of you, so that’s good!

  3. Mishi

    Made these for my grandfather’s birthday. The cookie parts are soooo perfect. <3 I love the consistency, and now the house smells like pumpkin... mmm... <3

  4. BeccaMarie

    How could I have not seen this post? I’ve never made whoopie pies, pumpkin would be a great place to start. Especially since we just pulled out nine pumpkins from our garden. Or maybe I’ll just used canned pumpkin. I don’t know. Can I make pumpkin puree out of a pumpkin? uuuuh, I don’t feel very smart right now…

  5. Jonie Marie

    Be still my heart. These look delicious! I think if I made them that I would eat the whole batch.

    Thanks for linking up to Point of View!

  6. bumblebee-bakes

    Made these tonight! The one change I made was that I doubled the amount of cinnamon in the filling because I’m a cinnamon lover. What a great recipe, thank you so much for sharing! This is the first time I’ve ever made whoopie pies (or had one!) and my family loved them.

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Bless This Mess - About Me

I’m Melissa, and I want to help you feed your family wholesome food.

As a hobby farmer and mom of five, I’m all about keeping it simple in the kitchen. I want healthy meals that feed my family well, and then I want to get back to my (messy) life. Let’s work together to find something yummy for your dinner table.

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