Pumpkin Whoopie Pies | Cookies and Cups

Homemade pumpkin whoopie pies are a festive fall dessert made from moist and tender pumpkin-shaped cookies filled with sweet cream cheese filling. 

These adorable pumpkin sandwich cookies are the perfect treat to make for Halloween, Thanksgiving, and beyond. If you love these, try my Apple Butter Whoopie Pies, too!

Easy Homemade Pumpkin Whoopie Pies

I have so many pumpkin desserts for fall, but today’s recipe is a little different. These pumpkin whoopie pies definitely put the “pumpkin” in “pumpkin dessert”, because they’re actually shaped like plump little pumpkins! This is a fun fall twist on whoopie pies made with creamy cream cheese filling sandwiched between soft and fluffy “orange velvet” cookies. These homemade pumpkin whoopie pies couldn’t be easier to make and they’re perfect for decorating, no matter the occasion.

Why You’ll Love This Pumpkin Whoopie Pie Recipe

• Soft, chewy sandwich cookies. These cookies are essentially chocolatey red velvet cookies, dyed pumpkin orange for fall. They’re melt-in-your-mouth soft, like little clouds wrapped around rich and tangy cream cheese frosting.
• Creamy filling. I fill these cookies with a variation of the cream cheese frosting from my carrot cake recipe. The creamy filling pairs perfectly with the chocolate and buttermilk flavors in the cookies.
• Easy to customize. Adapt the flavors of these whoopie pies and how you decorate them depending on the occasion. They’re great to make for Halloween, Thanksgiving, or any fall gathering.

Ingredients You’ll Need

Below are some notes on the ingredients you’ll need for the cookies and filling. Remember to scroll to the recipe card for the full amounts and recipe details.

• Flour
• Cocoa Powder: I recommend using a good-quality unsweetened natural cocoa powder.
• Baking Powder
• Butter: I recommend baking with unsalted butter. Remember to take the butter out of the fridge ahead of time, to let it come to room temperature.
• Brown Sugar: Light brown sugar gives the cookies a deeper, more caramelized flavor. Regular granulated sugar also works here, the flavor just won’t be quite the same.
• Egg and Vanilla
• Buttermilk: Buttermilk adds delicious tanginess and moisture to these orange velvet cookies. The acidity also reacts with the cocoa powder and baking powder, for light, soft, perfectly puffed cookies. If you don’t have buttermilk, see my post on how to make a buttermilk substitute.
• Food Coloring: You’ll need orange food dye for coloring the cookie batter, and any other colors you’d like for decorating. 

For the Cream Cheese Filling

• Cream Cheese and Butter: Take your cream cheese and butter out of the fridge ahead of time. Room-temperature ingredients are easier to mix.
• Vanilla
• Powdered Sugar: Also called confectioner’s sugar, powdered sugar thickens the filling.

How to Make Pumpkin Whoopie Pies

Get ready to whoop it up! Here’s how easy it is to make perfect pumpkin whoopie pies from scratch:

• Mix the wet and dry ingredients separately. Start by creaming together butter and sugar, followed by the egg and vanilla, and beat to combine. Mix the dry ingredients together in a separate bowl.
• Combine. Next, add the dry ingredients to the wet ingredients, alternating with buttermilk until smooth.
• Add food coloring. Add orange food coloring, a little at a time, to achieve your desired color. Gel food dyes are more potent, and you’ll need less color as a result. Mix the batter until the color is evenly distributed. 

• Pipe the pumpkin shapes. Now, transfer the orange cookie batter to a piping bag. You can also use a Ziploc bag with the corner snipped off. Gently pipe the batter out onto a baking sheet lined with parchment paper, creating “heart” shapes to resemble pumpkins. Be sure to leave about 2 inches between each pumpkin, to account for spreading.

• Bake. Bake your pumpkin cookies at 375ºF for 6 minutes. These cookies bake quickly, and you want to take them out while they’re still slightly underbaked. They should be just set, and still a little soft in the center.
• Cool. Leave the cookies to cool on the baking sheet for a minute or two before moving them to a wire rack. Make sure that the cookies are completely cooled to room temperature before filling them with frosting.

Filling the Whoopie Pies

Once your fluffy pumpkin-shaped cookies are baked and cooled, they’re ready for the cream cheese filling. Assembling these whoopie pies is easy to do:

• Make the frosting. Cream together butter and cream cheese until the mixture is smooth and fluffy. Slowly beat in powdered sugar until combined, then up the mixing speed and give the frosting a good whip. 
• Fill the cookies. Transfer the frosting to a piping bag (or another Ziploc bag). Flip one-half of the cookies so that their undersides are facing upward. Pipe a layer of frosting onto each cookie half, then press a second cookie over the frosting to form a sandwich.

Ways to Decorate Pumpkin Whoopie Pies

Once your pumpkin whoopie pies are assembled, you can get creative with ways to decorate! Here are some ideas:

• Pumpkin Stems: Broken mini pretzels make perfect little pumpkin stems! Break off pieces and press them into the filling at the top of your pumpkin whoopie pies to create “stalks”.
• Frosting: Make extra cream cheese frosting or a batch of regular buttercream frosting to use when decorating your whoopie pies. Color the frosting green to pipe cute little vines and leaves over each cookie.
• Jack-O-Lantern Cookies: For a fun Halloween variation, use black frosting to pipe spooky Jack-O-Lantern faces onto your pumpkin whoopie pies.
• Add-Ons: Use a small amount of frosting to adhere decorations like chocolate chips, M&Ms, or candy corn onto each cookie.

Recipe Tips and Variations

Follow these tips for the best pumpkin whoopie pies, plus some easy variations to try:

• Use room temperature ingredients. Room-temperature butter and cream cheese combine more smoothly with the other ingredients, and the cookies will bake more evenly as a result.
• Don’t overmix the batter. Over-mixing the batter can yield tough, dense cookies.
• Try to make the cookies as even-sized as possible. You can make these pumpkin whoopie pies as large or as small as you’d like, but make sure that the cookies are similar in size when you pipe them onto the baking sheet. This way each cookie will have two halves that match.
• Let the cookies cool completely before adding the filling. If the cookies are still warm, the cream cheese frosting will melt.
• To prepare these whoopie pies a day or two ahead, make the cookies and filling, and then store the components separately. You can assemble the pumpkin whoopie pies before serving. This way the cookies won’t get soggy or squished during storage.
• Add pumpkin spice. Add a teaspoon of pumpkin pie spice or ground cinnamon to the cream cheese filling. 
• Use another filling. You can fill these pumpkin whoopie pies with another flavor of frosting. Try my brown sugar frosting, or borrow the maple frosting from my pumpkin cake recipe. 

What to Serve with Pumpkin Whoopie Pies

These soft, fluffy pumpkin whoopie pies are a delicious treat with a warm mug of coffee, tea, or a cozy pumpkin spice hot chocolate in the afternoon. They’re also a fun dessert for Halloween parties, fall gatherings, and Thanksgiving. Here are some easy ideas:

How to Store

• Fridge: These pumpkin whoopie pies are fine to keep at room temperature if you’re serving them within 2 hours. Due to the cream cheese filling, however, it’s best to keep them refrigerated after that. Store them airtight for up to 3-4 days in the fridge.
• Freezer: Wrap your whoopie pies or store them airtight and keep them frozen for up to 3 months. Defrost the whoopie pies in the fridge before serving.

More Fall Baking Ideas 

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