Pumpkin Gingerbread Whoopie Pies

Featured in Delicious Desserts.

Combine the flavors of pumpkin spice and gingerbread in these soft sandwich cookies filled with cream cheese frosting. A delicious fall treat perfect for sharing.
Clare Greco
Updated on Tue, 21 Jan 2025 13:49:43 GMT
A plate of pumpkin spice sandwich cookies dusted with powdered sugar, featuring a creamy filling, is set against a background of autumn leaves and a pumpkin. Pin it
A plate of pumpkin spice sandwich cookies dusted with powdered sugar, featuring a creamy filling, is set against a background of autumn leaves and a pumpkin. | recipesim.com

Fall-Inspired Pumpkin Gingerbread Whoopie Pies

Let me share one of my absolute favorite fall treats with you - these incredible Pumpkin Gingerbread Whoopie Pies! I created these one cozy afternoon when I couldn't decide between making gingerbread or pumpkin cookies, and oh my goodness, am I glad I combined them! These little beauties are pure autumn magic soft, spiced cookies filled with the creamiest frosting you can imagine. Every time I make them, my kitchen fills with the most amazing aroma that brings everyone running to see what's in the oven!

Two Classic Flavors, One Amazing Treat

You know those recipes that just feel like a warm hug? This is definitely one of them! I've combined everything we love about pumpkin and gingerbread to create something truly special. The pumpkin keeps these cookies incredibly moist, while those warm gingerbread spices and a touch of molasses add such beautiful depth. Every time I bring these to a fall gathering, people beg for the recipe!

Let's Gather Our Ingredients

Here's everything you'll need to make these little pieces of heaven:

The Cookie Base:

  • All-purpose flour (nothing fancy needed!)
  • Baking soda for that perfect rise
  • A pinch of salt (trust me, it makes everything better)
  • My perfect spice blend (I use extra ginger!)
  • Unsalted butter, nice and soft
  • Light brown sugar for that caramel note
  • Farm-fresh eggs if you can get them
  • Real molasses (no substitutes here!)
  • Buttermilk for tenderness

For That Dreamy Filling:

  • The best cream cheese you can find
  • Pure vanilla (the good stuff!)

Let's Start Baking!

First things first - let's get that oven warming up to 350°F. While it's heating, I'll share my favorite trick: line your baking sheets with parchment. Trust me, it makes cleanup so much easier!

Now, let's mix our dry ingredients. I like to whisk them together really well - this ensures those warm spices are evenly distributed throughout every cookie.

Here comes the fun part! Cream that butter and brown sugar until it's light and fluffy. I usually set a timer for 3 minutes because I've learned the hard way that rushing this step never pays off!

Next, we'll add our wet ingredients one at a time. The molasses goes in beautiful streaks through the butter mixture before it all comes together. It's like watching fall happen right in your mixing bowl!

A plate of powdered sugar-dusted sandwich cookies filled with cream, with a pumpkin in the background. Pin it
A plate of powdered sugar-dusted sandwich cookies filled with cream, with a pumpkin in the background. | recipesim.com

The Perfect Bake

Now for my favorite part: scooping out those perfectly rounded cookies! I use a tablespoon measure to keep them all the same size (nobody wants mismatched whoopie pies!). Give each one a gentle pat with the back of your spoon - they'll spread just right as they bake.

Into the oven they go for 10-12 minutes. Your kitchen is about to smell amazing! You'll know they're done when they're just slightly firm to the touch but still soft in the middle. This gives us that perfect cake-like texture we're after.

Creating That Heavenly Filling

While your cookies cool (and yes, they must cool completely!), let's make that incredible cream cheese filling. This is where the magic happens! Beat your cream cheese until it's super smooth, then add powdered sugar and a splash of vanilla. I like to beat it for an extra minute to make it extra fluffy.

My secret? Let the filling chill for about 10 minutes before assembling your whoopie pies. It makes them so much easier to put together, and they look more professional too!

The Art of Assembly

Here's where patience pays off! Once your cookies are completely cool (and I mean completely no rushing this step!), it's time to create those perfect little sandwiches. I love this part! Put a generous dollop of filling on the flat side of one cookie, then gently press another on top. You'll see the filling spread to the edges that's when you know you've got it just right!

Let them rest for about 15 minutes before diving in. I know it's hard to wait, but this lets the filling settle and the cookies soften just slightly. Pure perfection!

Keeping Them Fresh

Want to know my storage secrets? These whoopie pies keep beautifully in an airtight container for up to 3 days though they rarely last that long in my house! If you need to store them longer, pop them in the fridge. Just let them come to room temperature before serving they're so much better that way!

Want to freeze them? Place them in a single layer in a container, and they'll keep for up to 3 months. It's like having a little taste of fall whenever you need it!

A plate of three cream-filled cookies, dusted with powdered sugar, is set against a cozy autumn backdrop with pumpkins and greenery. Pin it
A plate of three cream-filled cookies, dusted with powdered sugar, is set against a cozy autumn backdrop with pumpkins and greenery. | recipesim.com

Making Them Your Own

Over the years, I've discovered so many fun ways to customize these treats! Sometimes I'll fold mini chocolate chips into the batter, or add chopped crystallized ginger for extra zip. My kids love when I roll the edges in chopped pecans, and during the holidays, I've been known to swap the cream cheese filling for maple buttercream. Don't be afraid to experiment that's how the best recipes happen!

Perfect for Every Fall Gathering

These whoopie pies have become my signature fall dessert! I make them for Halloween parties (sometimes adding orange food coloring to the filling for fun!), Thanksgiving gatherings, and any cozy autumn get-together. There's something about that combination of pumpkin and gingerbread spices that just makes everyone feel warm and happy.

Baking With Little Helpers

One of my favorite things about this recipe is how perfect it is for baking with kids! My little ones love helping measure the spices and taking turns mixing the batter. The best part? Letting them sandwich the cookies together some turn out a bit messy, but those always seem to taste the best! It's such a wonderful way to create sweet memories in the kitchen.

The Science Behind the Magic

Want to know what makes these whoopie pies so incredibly soft and tender? It's all about that magical combination of molasses and buttermilk! The molasses adds moisture and helps keep the cookies soft for days, while the buttermilk reacts with the baking soda to create the most perfect, cake-like texture. Science can be delicious!

A plate of powdered sugar-dusted cream-filled cookies is displayed, surrounded by autumn-themed decorations. Pin it
A plate of powdered sugar-dusted cream-filled cookies is displayed, surrounded by autumn-themed decorations. | recipesim.com

Why These Are Extra Special

You know what makes these whoopie pies stand out? It's not just one thing it's how all the flavors work together in perfect harmony. That warm gingerbread spice, the subtle pumpkin, the tangy cream cheese filling every bite is balanced just right. Plus, they're substantial enough to feel like a real treat but not so sweet that you can't enjoy every last bite!

The Perfect Pairing

Let me tell you about my favorite way to enjoy these treat with a steaming mug of spiced apple cider! The warmth of the cider brings out all those beautiful spices in the cookies. Sometimes I'll brew a pot of chai tea instead the spices complement each other perfectly. On chilly afternoons, there's nothing better!

Make-Ahead Magic

Life gets busy, especially during fall, so I love that these can be made ahead! Sometimes I'll bake the cookies and freeze them unfilled, then just thaw and fill them when needed. It's such a time-saver during the holiday season. I've even been known to keep a batch in the freezer just for unexpected guests!

A Year-Round Treat

While these whoopie pies scream "fall," I'll let you in on a secret - they're amazing any time of year! During winter, I lean into those warm gingerbread spices a bit more. Come spring, I might add some orange zest to brighten things up. And in summer? A little extra vanilla in the filling makes them taste like ice cream sandwiches! The recipe is so versatile, it works in any season.

A platter of powdered sugar-dusted cookies filled with cream, set against a backdrop of autumn leaves. Pin it
A platter of powdered sugar-dusted cookies filled with cream, set against a backdrop of autumn leaves. | recipesim.com

Sharing the Love

These whoopie pies make the sweetest gifts! I love wrapping them individually in wax paper, then tucking them into pretty cellophane bags tied with ribbon. They're perfect for teacher gifts, welcome packages for new neighbors, or just because gifts. There's something so special about receiving a homemade treat, don't you think?

My Best Tips for Success

After making these countless times, here are my tried-and-true tips: Always, always use room temperature ingredients for the filling it makes such a difference in texture! Let those cookies cool completely before filling them (I know it's hard to wait!). And if you can't find pumpkin pie spice, make your own I actually prefer mixing my own blend, adding extra ginger and a pinch more cinnamon.

A Version for Everyone

Need to make these vegan? I've got you covered! Use flax eggs instead of regular eggs (1 tablespoon ground flax + 3 tablespoons water per egg), and grab your favorite plant-based cream cheese for the filling. I've even made them with coconut oil instead of butter they turn out beautifully! It makes me so happy knowing everyone can enjoy these special treats.

Bringing Fall Home

These Pumpkin Gingerbread Whoopie Pies have brought so much joy to my kitchen, and I know they will to yours too! They're more than just cookies they're little bites of fall that bring people together. Whether you're baking them for a special occasion or just because, they never fail to make people smile. And isn't that what baking is all about?

A close-up of powdered sugar-dusted sandwich cookies filled with cream, set against an autumn-themed backdrop featuring a pumpkin and colorful leaves. Pin it
A close-up of powdered sugar-dusted sandwich cookies filled with cream, set against an autumn-themed backdrop featuring a pumpkin and colorful leaves. | recipesim.com

Frequently Asked Questions

→ Can I make these ahead of time?
Yes, bake cookies ahead and store unfilled. Make filling when ready to serve. Once assembled, keep refrigerated for up to 3 days.
→ Why use buttermilk in the recipe?
Buttermilk adds moisture and tenderness to the cookies while its acidity helps activate the baking soda for proper rise.
→ Can I freeze these whoopie pies?
Unfilled cookies can be frozen for up to 2 months. Thaw completely before filling with fresh cream cheese frosting.
→ How do I store these?
Store assembled whoopie pies in an airtight container in the refrigerator due to the cream cheese filling.
→ How do I know when the cookies are done?
Edges should be golden brown but centers should still be slightly soft. They'll firm up as they cool.

Pumpkin Gingerbread Whoopie Pies

Soft gingerbread cookies with pumpkin pie spice, sandwiched around cream cheese frosting. A perfect blend of fall flavors in every bite.

Prep Time
30 Minutes
Cook Time
15 Minutes
Total Time
45 Minutes

Category: Delicious Desserts

Difficulty: Intermediate

Cuisine: American

Yield: 12 Servings (12 whoopie pies)

Dietary: Vegetarian

Ingredients

01 3 3/4 cups flour.
02 1 teaspoon baking soda.
03 1 teaspoon kosher salt.
04 3 teaspoons pumpkin pie spice.
05 3/4 cup unsalted butter, softened.
06 3/4 cup light brown sugar, packed.
07 1 large egg.
08 3/4 cup molasses.
09 3/4 cup buttermilk.
10 1/2 cup unsalted butter, softened (for filling).
11 6 ounces cream cheese, softened.
12 2 1/2 cups powdered sugar.
13 1/4 teaspoon pure vanilla extract.

Instructions

Step 01

Heat oven to 350°F. Line baking sheet with parchment. Mix dry ingredients in bowl.

Step 02

Beat butter and sugar until fluffy. Add egg. Mix in molasses and buttermilk alternating with dry ingredients.

Step 03

Drop tablespoons of batter on baking sheet. Bake 10-12 minutes until edges are golden but centers soft.

Step 04

Beat butter, cream cheese, powdered sugar and vanilla until stiff peaks form.

Step 05

Match cookies by size. Pipe filling on bottom cookie and top with matching cookie.

Notes

  1. Let cookies cool completely before filling.
  2. Use piping bag for neat filling.
  3. Store in refrigerator.

Tools You'll Need

  • Electric mixer.
  • Baking sheets.
  • Parchment paper.
  • Piping bag with tip.

Allergy Information

Please check ingredients for potential allergens and consult a health professional if in doubt.
  • Dairy.
  • Eggs.
  • Wheat.

Nutrition Facts (Per Serving)

It is important to consider this information as approximate and not to use it as definitive health advice.
  • Calories: 588
  • Total Fat: 25 g
  • Total Carbohydrate: 86 g
  • Protein: 6 g