Easy Chocolate Pumpkin Whoopie Pies for Fall

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If you are craving a sweet fall dessert, these decadent Chocolate Pumpkin Whoopie Pies will leave you satisfied. Fluffy dark chocolate cookie cakes with rich pumpkin spiced cream cheese filling make the perfect fall treat for a Halloween party, Fall Barn party, or Autumn gift basket.

Why you’ll love this recipe:

CROWD PLEASER. The whoopie pie might be the perfect treat…you can customize the flavors like any cake or cupcake, but it’s also an easy hand-held dessert that doesn’t require a plate and fork. They aren’t fussy or pretentious. And they are loved by both children and grown-ups alike. This makes them the ultimate party treat in my opinion. They are fun to make and always a crowd-pleaser.

HALLOWEEN TREAT: They are a perfect Halloween treat with the iconic orange and (almost) black colors. You can even cut the cookie cake to make Jack-O-Lantern faces that will delight kids (and adults).

What is a Whoopie Pie?

If you’ve never had one of these delectable treats then you are in for a sweet surprise. A traditional whoopie pie consists of a chocolate cake-like cookie top and bottom and a marshmallow cream filling. Over the years many bakers have created whoopie pies with different flavored cookie-cakes and flavored cream fillings, including buttercream and cream cheese-based fillings.

Who invented the Whoopie Pie?

The Whoopie Pie hails from New England and Amish country, with several states including Maine, Massachusetts, and Pennsylvania all claiming to be the originator of the whoopie pie, but there doesn’t seem to be conclusive evidence as to who made the first one. It seems to date back to the early 1920s, with a Maine bakery claiming they have been making it since 1925. Regardless of who invented it, it was a great invention that has grown in popularity over the last three decades mainly due to the internet.

If you want to try a variety of whoopie pies in one place, a great event to visit would be the Whoopie Pie Festival at the Hershey Farm in Ronks, PA. They have been hosting a Whoopie Pie festival for nearly 20 years. It’s a hoot!

Fun fact: In western Pennsylvania area they are called Gobs, not Whoopie Pies.

What is Whoopie Pie filling made of?

The most common fillings are marshmallow cream, vanilla buttercream, and cream cheese filling. I do really like marshmallow cream, but to be honest I love the cream cheese filling the best. It’s not as sweet and adds a rich creamy decadence to the dessert. Just don’t count calories folks.

What are some other good Whoopie Pie flavors?

While I am partial to this Einkorn Chocolate Pumpkin Whoopie Pie flavor…There are so many different variations you can try. These are easily customizable with the filling or the shell. Some great combinations include:

• Chocolate Shell with maple filling
• Chocolate shell with a fruit filling (raspberry, strawberry, banana)
• Chocolate shell with butter pecan filling
• Pumpkin Shell with vanilla spice filling
• Peanut Butter shell with chocolate filling
• Vanilla shell with lemon filling
• Vanilla shell with peanut butter and jelly filling.

You can also get creative and add chopped nuts or candies to your filling.

What size should a Whoopie Pie be?

A traditional whoopie pie is about 4” in diameter. If you use a 2 oz. scoop you will get cookie cakes that measure about 4” in diameter. This scoop also makes it super easy to dispense the sticky batter onto your baking sheet.

If you want smaller bite-sized whoopie pies then I would recommend using a small cookie scoop like the Nordic Ware cookie scoop. This will yield cookie cakes that are about 2”-2.5” in diameter.

You can see the size difference below:

Tools you need to make Chocolate Pumpkin Whoopie Pies:

• Mixing Bowls
• A Stand Mixer. I use a classic KitchenAid. I’ve had it for years and is a worthwhile investment if you love to bake.
• Spatula
• Portion Scoop. I use a 2oz. portion scoop for 4″ round whoopie pies.
• Baking Sheet. I use Nordic Ware baking sheets and highly recommend them.

Ingredients you need to make Chocolate Pumpkin Whoopie Pies:

For the cookie cakes:

• Unsalted Butter. Room temperature.
• Dark Brown Sugar
• Eggs
• Buttermilk. In a pinch you can also use regular milk, I recommend whole milk for added richness.
• Vanilla Extract
• Dutch Process Cocoa. You can also use regular cocoa, it just won’t have the intense chocolate flavor and will be lighter in color.
• Flour. I use Einkorn flour from Jovial Foods, but you can also use regular All-purpose flour.
• Baking Soda
• Baking Powder
• Salt
• Cinnamon

For the filling:

• Cream Cheese. Room temperature.
• Powdered Sugar
• Unsalted Butter. Room temperature.
• Pumpkin Puree
• Cinnamon, Ginger and Nutmeg

How to make Chocolate Pumpkin Whoopie Pies:

To make the cookie cakes:

1. Preheat your oven to 350°
2. In a large bowl cream the butter and brown sugar together for about 2 minutes. Add the egg and mix to combine.
3. In a separate bowl combine the cocoa, Einkorn flour, baking powder, baking soda, cinnamon, and salt.
4. In a small bowl mix your buttermilk and vanilla together.
5. Add the dry ingredients to the butter mixture, alternating with the buttermilk mixture, beating until smooth. Be careful not to overmix.
6. Drop batter by ¼ cup onto prepared baking sheets. This scoop makes it easy. This will yield 4” diameter cookie cakes. Alternatively, you can use a 1-1/2 Tbsp cookie scoop for 2”-2.5” diameter cookie cakes.
7. Be sure to leave at least 2” of space between each scoop of batter so they have room to spread.
8. From here you can either bake them as is or spread the batter out a bit with the back of a spoon. If you do this, they will be slightly flatter and have a smoother top. If you don’t do this they will turn out a bit more mounded on top with some cracks. I think they look great either way!
9. Bake for 15-16 minutes or until they are firm to the touch. Remove from oven and cool on baking sheet for a few minutes before transferring to a wire rack to cool completely.

In the image below you can see that the two bottom cookie cakes were smoothed slightly with a spoon before baking, giving them a slight smoother appearance. If you leave them as is they will get that “cracked” top, which I personally prefer.

To make the filling:

1. Beat the cream cheese and butter in a bowl until well combined.
2. Slowly beat in the powdered sugar until smooth.
3. Add the pumpkin puree, cinnamon, ginger, and nutmeg and mix until combined.

Assembling the Whoopie Pies:

Use a small cookie scoop to add 1 to 2 scoops of filling onto the flat side of a cookie cake. Place the flat side of another cookie cake on top and press down gently to sandwich them together.

Note, 1 scoop of filling is good, but 2 scoops will make them nice and plump. It’s really up to you how much you want and how you want them to look. You can see the difference in my photos.

If you are making the smaller bite-sized whoopie pies, then 1 scoop is perfect for a nice plump whoopie pie.

How do I store the Einkorn Chocolate Pumpkin Whoopie Pies?

They can be set out at room temperature for a few hours. After that they are best wrapped individually in plastic wrap and stored in the fridge. This way they won’t stick to each other. They will keep fresh in the fridge for up to a week.

To freeze, just put the wrapped pies in a freezer-tight bag and freeze for up to one month.

Happy Baking!

-Jessica

More Halloween Recipes:

• The BEST Reese’s Pieces Peanut Butter Cookies!
• Halloween Tequila Drinks-Headless Horseman Black Margarita
• Irresistible Halloween Caramel Popcorn
• 3 Spooky Gin Halloween Cocktails