Pumpkin Whoopie Pies with a Whipped Cinnamon Filling
Updated Jan 09, 2025
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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.
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.
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!
Table of Contents
Why You’ll Love This Recipe
- Pumpkin whoopie pie cookies are deliciously sweet and wickedly adorable cookie sandwiches that are easy-to-make desserts to ring in autumn.
- 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!
Recipe Ingredients
- Butter
- Sugar – you’ll need both regular granulated and powdered sugars
- Eggs
- Pumpkin puree
- Vanilla extract – I really like using vanilla bean extract
- Flour
- Baking powder
- Baking soda
- Cinnamon
- Whipping cream – this is heavy cream, sometimes called whipping cream
See the recipe card below for full information on ingredients and quantities.
How to Make Pumpkin Whoopie Pies
- Beat the butter and sugar, then add eggs, pumpkin, and vanilla.
- Add in dry ingredients and mix until well incorporated.
- Scoop onto baking sheet and bake. Let cool.
- Mix filling ingredients and spread onto one-half of cooled cookies, topping with rest of cookies.
Recipe FAQs
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!”
Bake the cookies and allow to cool. 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!”
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.
Expert Tips
- 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.
- To keep the whoopie pies from sticking, use parchment paper to bake them. If you experience stuck cookies to the parchment paper, you could also spray the parchment paper lightly with canola oil cooking spray.
- 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.
- If you’re a fan of pumpkin-flavored sweet treats, I’ve got a full list of yummy confections you MUST try. Here are a few of my favorites: Cake Mix Pumpkin Chocolate Chip Cookies, Perfect Pumpkin Bread, and Extra Thick Pumpkin Cake. Yum yum!
More Cookie Recipes To Consider
Oatmeal Cookies
Oatmeal Coconut Cookies With Dark Chocolate Chunks
Oatmeal Cookies
Oatmeal Cowboy Cookies Recipe
Simple Gingerbread Recipes
Perfect Iced Gingerbread Cookies
Chocolate Chip Cookies
Mason Jar Chocolate Chip Cookie Recipe
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Pumpkin Whoopie Pies with a Whipped Cinnamon Filling
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
- Preheat the oven to 350 degrees F.
- 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.
- Add the eggs, and mix to incorporate.
- Add the pumpkin and vanilla, and mix to combine.
- 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.
- Using a one-ounce scoop, scoop the batter onto a parchment lined baking sheet, spacing them 2 inches apart.
- Bake for 10 to 12 minutes, until the cookie springs back slightly when touched.
- 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.
- Add the powdered sugar, and beat for another 3 to 5 minutes. The filling will be very fluffy and a medium-thin consistency.
- 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.
- 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.
- To keep the whoopie pies from sticking, use parchment paper to bake them.
- 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.
Not a huge fan of pumpkin so will sweet potato work instead?
I think they might be a little too heavy for this recipe… or just whip them up really good and then measure. I’d sure try it though, if you get flat cookies though, you’ll know why.