The Best Soft & Easy Pumpkin Whoopie Pies

Imagine a soft, pillowy, and deeply chocolatey cake-like cookie, sandwiched together with a luscious, creamy, and perfectly spiced pumpkin cream cheese filling. These incredible, from-scratch Pumpkin Whoopie Pies are the ultimate handheld fall treat, and they are so much fun to make! This is the perfect dessert for any autumn celebration, from a Halloween party to the Thanksgiving dessert table.

This isn’t just a recipe; it’s your guide to creating the perfect fall “dessert sandwich.” We’ll show you the simple secrets to an incredibly soft and tender chocolate cookie, and a smooth, tangy pumpkin spice filling that is the stuff of dreams. Forget complicated layer cakes or fussy pies; these easy, individual treats are guaranteed to be a massive hit with both kids and adults.

Table of Contents

Table of Contents

Recipe Overview: The Perfect Handheld Fall Treat

What makes these Pumpkin Whoopie Pies so spectacular is their perfect combination of a soft, cakey chocolate cookie and a rich, tangy pumpkin cream cheese filling. A whoopie pie is a classic American dessert, and this version gives it a wonderful, festive, autumnal makeover. The recipe is wonderfully simple, using classic baking techniques to create a show-stopping result. Best of all, they are a fantastic make-ahead treat, perfect for stress-free party planning.

Metric	Time / Level
Total Time	1 hour 30 minutes (plus cooling time)
Active Prep Time	25 minutes
Difficulty Level	Easy
Servings	12 whoopie pies

The Essential Ingredients for This Festive Treat

This recipe is made from two delicious, from-scratch components.

• The Soft Chocolate Whoopie “Pies”: These are not pies at all, but wonderfully soft, tender, and cake-like cookies.
  • Buttermilk: This is a key ingredient for the signature texture of a classic whoopie pie. The acidity in the buttermilk reacts with the leaveners to create an incredibly soft, tender, and moist crumb with a subtle, pleasant tang.
  • Unsweetened Cocoa Powder: A good quality cocoa powder provides a rich, deep chocolate flavor that is the perfect, classic complement to the pumpkin spice filling.
  • Room Temperature Ingredients: It is crucial that your butter and eggs are at room temperature. This is the secret to the “creaming method,” which creates a smooth, emulsified batter and a wonderfully light and even cookie crumb.
• The Creamy Pumpkin Cream Cheese Filling: The rich, sweet, and tangy swirl in the center.
  • Room Temperature Ingredients: This is the non-negotiable secret to a perfectly smooth, lump-free cream cheese filling. Your full-fat, block-style cream cheese and your unsalted butter must both be fully softened to room temperature before you begin.
  • Pure Pumpkin Purée: Be sure to use 100% pure pumpkin purée, not pre-sweetened and spiced pumpkin pie filling. This provides the authentic pumpkin flavor and beautiful orange color.
  • Ground Cinnamon: A touch of ground cinnamon gives the filling that classic, warm “pumpkin spice” flavor.

Step-by-Step to the Perfect Pumpkin Whoopie Pies

This is a fun and rewarding baking project. Follow these detailed steps for a perfect result.

Part 1: Bake the Soft Chocolate Whoopie Pie Cookies

Step 1: First, preheat your oven to 400°F (200°C). Line three large baking sheets with parchment paper.

Step 2: In a large bowl of a stand mixer fitted with the paddle attachment, or in a large bowl with a hand mixer, beat the 1 stick of room temperature butter and the 1 1/4 cups of granulated sugar together until the mixture is light and fluffy.

Step 3: Beat in the 1 large egg, and then the 1 cup of room temperature buttermilk and the 1 teaspoon of pure vanilla extract.

Step 4: In a separate medium bowl, whisk together the 1 3/4 cups of all-purpose flour, the 3/4 cup of unsweetened cocoa powder, the 1 1/2 teaspoons of baking soda, the 1/2 teaspoon of baking powder, and the pinch of kosher salt.

Step 5: With the mixer on a low speed, gradually add the dry ingredients to the wet ingredients and mix only until the batter is just combined and smooth. Do not overmix.

Step 6: Using a 2-tablespoon cookie scoop for uniform size, drop 8 scoops of the soft batter onto each of your prepared baking sheets, making sure to space them about 3 inches apart as they will spread.

Step 7: Bake for about 8 minutes. The cookies are perfectly done when the edges are set, but the centers are still very soft.

Step 8: Let the cookies cool on the baking sheets for about 2 minutes before you carefully transfer them to a wire rack to cool completely.

Part 2: Whip Up the Pumpkin Cream Cheese Filling

While the cookies are cooling, you can make the delicious pumpkin filling.

Step 1: In a small bowl, using an electric mixer, beat the 4 ounces of room temperature cream cheese and the 4 tablespoons of room temperature butter together until they are completely smooth.

Step 2: With the mixer on a low speed, slowly beat in the 2/3 cup of confectioners’ sugar until it is smooth.

Step 3: Add the 1/4 cup of canned pure pumpkin, the 1/4 teaspoon of ground cinnamon, and the pinch of kosher salt. Beat the mixture until it is smooth and well combined.

Part 3: Assemble Your Whoopie Pies

Once your chocolate cookies are completely cool, you can assemble your whoopie pies.

Turn half of the cookies (12 of them) over so that their flat, bottom side is facing up.

Spread a heaping tablespoonful of the prepared pumpkin cream cheese filling on the flat side of each of those 12 cookies.

Gently sandwich the filling with a second cookie, with its flat side down, pressing gently to spread the filling to the edges. Repeat this process with the remaining cookies and filling.

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Storage and Make-Ahead Tips

These Pumpkin Whoopie Pies are a fantastic treat to make ahead for a party or a holiday.

• Make-Ahead: You can make all the components separately in advance. The baked cookies can be stored in an airtight container at room temperature for up to 2 days. The pumpkin cream cheese filling can be made up to 3 days in advance and stored, covered, in the refrigerator.
• Storage: The finished, assembled whoopie pies must be stored in an airtight container in the refrigerator because of the cream cheese filling. They will stay fresh and delicious for up to 4 days.
• Serving: For the absolute best flavor and texture, it is a great idea to remove the whoopie pies from the refrigerator and let them sit at room temperature for about 20-30 minutes before serving. This allows the cookies to soften slightly and the flavors of the filling to shine.

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Creative Recipe Variations

This fun and festive cookie is a wonderful base for your own delicious and creative twists.

1. Add a Classic Chocolate Chip Kick: For an even more decadent, double-chocolate treat, you can gently fold 1 cup of mini semi-sweet chocolate chips into the cookie batter at the very end.
2. Add a Festive Decorative Touch: For a fun and beautiful presentation, you can gently roll the exposed edges of the cream cheese filling of each assembled whoopie pie in some festive fall-themed sprinkles or some finely chopped, toasted pecans.
3. Make it a Classic Whoopie Pie: If you’re not in the mood for pumpkin, you can create a classic, traditional whoopie pie by simply omitting the pumpkin and the cinnamon from the filling and increasing the vanilla extract to 1 teaspoon.

Enjoy Your New Favorite Fall Treat!

You’ve just created a wonderfully fun, creative, and delicious cookie that is sure to be the star of your fall baking season. These Pumpkin Whoopie Pies are a perfect harmony of a soft, cakey chocolate cookie and a rich, creamy, and spiced filling. It’s a sweet and simple way to celebrate the cozy flavors of the season in a perfect, individual-sized package.

We hope you and your family love making—and eating—this delicious new tradition!

If you enjoyed making this recipe, please leave a comment below or share it with a friend who is looking for a fun fall baking project!

Frequently Asked Questions (FAQs)