Pumpkin Pie Whoopie Pies – The Ultimate Fall Dessert You Can’t Miss

Introduction

Pumpkin pie whoopie pies are the cozy, spiced-up treats you didn’t know you needed this fall. Imagine soft pumpkin cookies sandwiching a dreamy cream filling — it’s like pumpkin pie and whoopie pies had the sweetest baby. These seasonal delights are quickly becoming a go-to dessert for fall parties, Thanksgiving tables, and weekend baking adventures.

In this guide, we’re diving deep into everything you need to know about making and enjoying pumpkin pie whoopie pies. From their tasty origin story and best ingredient combinations to pro baking tips, healthy swaps, and creative ways to serve them — we’re covering it all. You’ll even learn how to fix common issues like stickiness and dryness and how to store them so they stay as fresh as the day you made them.

Looking for inspiration? Try this delicious whoopie pie guide to explore the roots of this classic dessert before we twist it with pumpkin flair. Looking for more cozy fall dessert ideas? Follow us on Facebook for daily inspiration!

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What Are Pumpkin Pie Whoopie Pies?

A Delicious Twist on Classic Whoopie Pies

Pumpkin pie whoopie pies are a seasonal spin on the traditional whoopie pie — a dessert made by sandwiching a creamy filling between two cake-like cookies. Instead of the usual chocolate or vanilla base, this fall-friendly version features soft, spiced pumpkin cakes that taste just like a slice of pumpkin pie in cookie form.

The filling often mirrors the flavors of pie, too. Cream cheese frosting, cinnamon-infused marshmallow cream, or even pumpkin spice buttercream take these treats over the top. These whoopie pies are soft, moist, and packed with warm autumn spices like cinnamon, nutmeg, and cloves, delivering that nostalgic flavor you crave during the cooler months.

This dessert is the perfect hybrid: portable like a cookie, fluffy like cake, and comforting like pie.

How Pumpkin Spice Transforms the Treat

What makes pumpkin pie whoopie pies truly special is the addition of pumpkin puree and warm spices to the batter. Not only does pumpkin add natural moisture and softness to the cookies, but it also enhances the flavor with its sweet, earthy profile.

Pumpkin spice — a blend typically made of cinnamon, ginger, nutmeg, allspice, and cloves — turns a plain cookie sandwich into a full-on fall flavor bomb. Thanks to the moisture-rich pumpkin, these cookies stay incredibly soft and pillowy—each bite feels like it’s melting right on your tongue.

That’s why these seasonal gems are more than just a novelty — they’re a must-bake tradition once sweater weather hits.

History of Whoopie Pies and Pumpkin Variations

Origins of the Whoopie Pie

Pumpkin pie whoopie pies are a seasonal twist on a dessert that’s been around for decades. Traditional whoopie pies — soft chocolate cake cookies filled with creamy marshmallow or buttercream — originated in New England and Pennsylvania. Amish women are credited with baking them and placing them in lunch pails, with children shouting “Whoopie!” upon finding them.

Over time, the classic treat evolved into a dessert canvas, allowing for all kinds of fun flavor combinations. Maine even declared the whoopie pie its official state treat, and this guide to Maine’s version is a great read for whoopie pie lovers.

The Rise of Pumpkin pie whoopie pies Inspired Desserts

Pumpkin spice took over the fall season thanks to its rich, cozy flavor. Bakers started incorporating pumpkin puree and pie spices into cookies, cakes, and yes — whoopie pies. It was a natural pairing. The soft texture of pumpkin cake layers and the sweet, spiced filling mimic everything we love about traditional pumpkin pie but in handheld form.

Now, pumpkin pie whoopie pies have become a fall favorite, merging nostalgia with seasonal flavor. Whether filled with cream cheese frosting, maple fluff, or cinnamon buttercream, they offer that perfect taste of autumn in every bite.

Ingredients Breakdown for the Perfect Pumpkin Pie Whoopie Pies

Best Pumpkin Puree and Spice Blends to Use

For moist and flavorful pumpkin pie whoopie pies, the key is starting with high-quality pumpkin puree. Skip the pumpkin pie filling, which contains added sugars and spices, and opt for pure canned pumpkin. It delivers the right texture and flavor without making your batter too runny.

As for spices, a blend of cinnamon, nutmeg, ginger, and cloves gives these treats that classic fall aroma. Many bakers use store-bought pumpkin pie spice, but mixing your own lets you control the balance. Just a pinch of allspice or cardamom can make your recipe stand out.

Pairing that spiced batter with brown sugar adds richness, while a touch of vanilla brings the whole flavor profile together.

Cream Cheese Filling vs Marshmallow Cream Debate

The filling can make or break your Pumpkin pie whoopie pies. Cream cheese frosting is the most popular for pumpkin versions — it’s tangy, smooth, and balances the sweetness of the cookies. Add a little cinnamon or maple syrup for depth.

On the other hand, marshmallow fluff gives a lighter, more nostalgic feel. It’s sweeter, airier, and mimics traditional whoopie pie filling. Some bakers even blend the two for a rich yet fluffy center.

Whichever you choose, be sure to chill the filling slightly before assembling. This prevents it from oozing out and keeps the sandwiches clean and easy to eat.

Discover great ideas like this fall-favorite pink salt recipe that pairs well with dessert season.

Step-by-Step Recipe for Homemade Pumpkin Pie Whoopie Pies

Making the Soft Pumpkin pie whoopie pies Layers

Start by preheating your oven to 350°F (175°C) and lining two baking sheets with parchment paper. In a large mixing bowl, whisk together your dry ingredients: all-purpose flour, baking soda, baking powder, salt, cinnamon, nutmeg, ginger, and cloves.

In another bowl, blend brown sugar, granulated sugar, and vegetable oil until smooth. Add in eggs, pumpkin puree (not pumpkin pie filling), and vanilla extract. Gradually mix in the dry ingredients until just combined — don’t overmix or your cakes will turn dense.

Use a cookie scoop to drop even portions of batter onto the baking sheets, spacing them out to allow spreading. Bake for 10–12 minutes until the cakes are puffed and spring back lightly when touched. Let them cool completely before filling.

Preparing the Creamy Pumpkin pie whoopie pies Inspired Filling

For a classic filling, beat softened cream cheese and unsalted butter until fluffy. Add powdered sugar a little at a time, then a splash of vanilla and a pinch of cinnamon. You can also stir in maple syrup or a touch of pumpkin spice to deepen the flavor.

Prefer something lighter? Whip marshmallow fluff with shortening and vanilla for a nostalgic touch.

Once your cakes are cool, pipe or spoon the filling onto the flat side of one cookie and gently press another on top to form a sandwich. Chill in the fridge for 20–30 minutes so they set properly.

Don’t miss our detailed post on whoopie pie traditions if you want to explore more styles and flavors!

Tips for Baking Soft and Moist Whoopie Pies

Avoiding Dry or Gummy Cakes

The texture of your pumpkin pie whoopie pies hinges on just a few key details. First, don’t overmix the batter — that can lead to tough or rubbery cakes. Gently mix until you no longer see any streaks of flour in the batter.

Next, measure your flour accurately using the spoon-and-level method. Too much flour will dry out the cakes, while too little may make them spread too much and become flat or gummy.

Pumpkin puree adds moisture, but too much of it can lead to dense cakes. Stick to the recipe amounts and avoid watery puree. Also, check your oven temperature with a thermometer; even 10 degrees off can change the texture.

Finally, remove the cakes from the oven when they’re just set. Overbaking dries them out quickly. They should spring back lightly when touched.

Why Pumpkin pie whoopie pies Turn Sticky and How to Fix It

Sticky tops are a common issue, especially with pumpkin-based batters. High humidity or underbaking can leave moisture on the surface. To reduce stickiness, allow your cakes to cool completely on a wire rack.

You can also refrigerate or briefly freeze them after cooling, which helps the tops set and makes assembly easier.

If your whoopie pies stay sticky no matter what, a light dusting of powdered sugar (right before serving) can keep them from sticking to each other in storage containers.

Discover more baking hacks in our fall-flavored dessert recipes.

Are Pumpkin Pie Whoopie Pies Healthy or Indulgent?

Nutritional Breakdown and Ingredient Swaps of Pumpkin pie whoopie pies

Let’s be real — pumpkin pie whoopie pies are a treat. But that doesn’t mean you can’t make smarter choices when baking them. A traditional recipe contains flour, sugar, butter or oil, pumpkin puree, and a rich filling — all of which add up to a sweet indulgence.

However, you can lighten them up without sacrificing flavor. Swap white flour for whole wheat pastry flour or oat flour to add fiber. Replace some of the oil with unsweetened applesauce or Greek yogurt to reduce fat and add moisture. Use pure maple syrup or coconut sugar instead of refined white sugar for a more natural sweetness.

Pumpkin itself is a healthy ingredient — it’s low in calories, rich in fiber, and packed with vitamin A. So, while the dessert overall isn’t “diet food,” it’s certainly better than many processed sweets.

Healthier Alternatives Without Losing Flavor

Want a more guilt-free version? Try a dairy-free filling using whipped coconut cream and a bit of powdered monk fruit sweetener. Or make mini whoopie pies — you still get the flavor but in a smaller, portion-controlled bite.

You can also skip the top layer entirely and serve a single pumpkin cake round with a dollop of filling like an open-faced cookie sandwich. It’s a fun, modern take that reduces sugar and carbs.

Looking for inspiration? Try this detox-friendly pink salt recipe as a refreshing follow-up to dessert.

Serving Ideas for Pumpkin Pie Whoopie Pies

Holiday Presentation and Gifting Tips

Pumpkin pie whoopie pies are show-stoppers on any fall dessert table, especially when you dress them up a bit. Dust them with powdered sugar, drizzle with maple glaze, or roll the edges in crushed pecans for an elegant touch. For parties, stack them on a tiered cake stand or place each one in a decorative cupcake liner.

Want to gift them? Wrap each whoopie pie in parchment paper or place them in clear cellophane bags with twine and a fall-themed tag. They make thoughtful hostess gifts, bake sale items, or treats for coworkers and neighbors.

Creative Pairings and Toppings to Try

These pumpkin treats shine on their own, but they also pair beautifully with other fall flavors. Serve them with hot apple cider, spiced chai, or cinnamon latte. For a fun twist, add a smear of apple butter to the filling or sprinkle in some mini chocolate chips.

Toppings like candied ginger, a caramel drizzle, or even crushed graham crackers can add new textures and flavor dimensions. Some bakers even turn them into frozen treats by adding a scoop of vanilla bean ice cream between the layers, then freezing them for 30 minutes.

Don’t miss our guide to whoopie pie origins for more creative inspiration on serving and styling these nostalgic goodies.

Storage, Freezing, and Shelf Life Explained

How to Keep Them Fresh Longer

To keep your pumpkin pie whoopie pies soft, moist, and fresh, proper storage is key. Once assembled, store them in an airtight container with parchment paper between layers to prevent sticking. Keep the container in the refrigerator to extend freshness — they’ll last up to 5 days this way.

If you plan to serve them the same day, you can store them at room temperature for up to 6–8 hours. However, because of the cream-based filling, refrigeration is always safer, especially if you’re using cream cheese.

Let them sit at room temperature for about 20 minutes before serving to bring out the best texture and flavor.

Best Ways to Freeze and Thaw Properly

Want to make your whoopie pies ahead of time? No problem. Freeze the cookies and filling separately, or freeze them fully assembled. If freezing assembled, wrap each pie individually in plastic wrap, then store them in a freezer-safe bag or container.

You can store them in the freezer for up to two months without losing quality. To thaw, unwrap and place them in the refrigerator overnight or let them sit at room temperature for 30–60 minutes. Avoid microwaving them — it ruins the texture.

Freezing not only helps you prep in advance for holidays but also lets you portion out treats for when the cravings hit.

Pumpkin Pie Whoopie Pies Around the Web

Trending Variations and Instagram-Worthy Versions

If you’ve scrolled through fall baking hashtags, you’ve likely spotted dozens of dreamy pumpkin pie whoopie pies. From mini versions perfect for entertaining to oversized, bakery-style giants stuffed with maple cream — the variations are endless.

Food bloggers have added all kinds of creative twists. Some incorporate browned butter into the batter for a richer, nutty flavor. Others roll the filling edges in crushed candied pecans, mini white chocolate chips, or even graham cracker crumbs for added crunch and visual appeal. For a grown-up version, try bourbon-spiked cream filling — a hit at Friendsgiving parties.

These viral takes aren’t just about taste — they’re styled for social media, too. Piped fillings, decorative drizzle, and coordinated fall-themed props help them steal the spotlight on Instagram and Pinterest. Want even more seasonal dessert creativity? Check out our favorite pins on Pinterest to discover new takes on pumpkin pie whoopie pies!

Where to Buy or Order Online

Not in the mood to bake? You can still get your fix. Many artisan bakeries, especially in the Northeast, sell pumpkin pie whoopie pies during the fall season. Online stores like Etsy, Goldbelly, or local farm shops offer nationwide delivery — just search for seasonal whoopie pies.

Pro tip: Buy early. Limited-edition fall flavors sell out fast, especially in October and November. Whether you’re treating yourself or sending a gift, they arrive fresh and ready to enjoy.

Frequently Asked Questions About Pumpkin Pie Whoopie Pies

What is a pumpkin whoopie pie?

It’s a soft, spiced pumpkin cookie sandwich filled with cream — like pumpkin pie in a handheld dessert form.

What is a whoopie pie made of?

A classic whoopie pie includes two soft cake-like cookies and a sweet filling, often marshmallow or cream cheese.

Why are my pumpkin whoopie pies sticky?

They’re likely underbaked or stored while warm. Cool completely and separate with parchment to avoid stickiness.

Is pumpkin pie healthy or unhealthy?

Pumpkin is healthy, but sugar and cream fillings add calories. Use swaps like Greek yogurt or less sugar for a lighter version.

Conclusion and Final Thoughts

Pumpkin pie whoopie pies are the perfect blend of tradition and seasonal flavor. With soft pumpkin-spiced cookies and rich, creamy filling, they bring together everything we love about fall desserts in one indulgent bite. Whether you bake them from scratch, customize the filling, or gift them to friends and family, these little pies always deliver big on comfort and flavor.

Ready to try your hand at more nostalgic sweets? Check out our guide to classic whoopie pies in Maine for even more inspiration.