Pumpkin Whoopie Pies with Cinnamon Cream Cheese Filling

I know I know…you are saying to yourself, not another pumpkin recipe, but I PROMISE you…this recipe is one of the best things you will ever taste!!  As you guys already know, I am a pumpkin nut and this time of year makes me super happy about the holidays to come and all of the seasonal flavors!! 🙂  Something about whoopie pies also make me really happy.  They are the perfect little dessert package and are just the right size so that you don’t feel like you have over indulged!

I absolutely love these treats and am so excited about how the recipe turned out.  I decided to add some pumpkin pie spice to boost the flavor a bit, and it really gave the whoopies a lovely taste.  Also creating a super rich, cinnamon spiked, cream cheese frosting was the perfect accompaniment to these little bites of heaven.  The recipe make a lot, and they actually get better as a few days go by, so make them and go to town…or freeze the leftovers after a few days so that they can stay fresh. Happy Fall everyone!!

Super yummy ingredients.

I decided to add some milk to the batter after the fact because I needed to thin it out a bit!

After scooping the batter onto the silpats, I smoothed the tops with my finger.  It’s not necessary unless you want them very round.

They bake up so yummy and make the house smell SO good 🙂

The recipe makes a lot so invite lots of friends over…or just pretend like you’re at a party and you don’t have to share 🙂

This frosting is dangerously delicious!

Now who can say no to this?

They are so luscious!

How beautiful is this?

They make a perfect hostess gift!

Don’t you just want to bite the screen? 🙂

Go ahead…treat yourself 🙂

Pumpkin Whoopie Pies with Cinnamon Cream Cheese Filling

Makes: 26 whoopie pies Prep time: 25 minutes Bake time: 9 to 12 minutes



1 cup softened, unsalted butter

2 cups packed Dixie Crystals Brown Sugar

2 large eggs

1, 15 ounce can pumpkin puree

1/4 cup whole milk

1 teaspoon vanilla extract, I use Nielsen Massey Madagascar Bourbon Vanilla

1 and 1/2 teaspoons cinnamon

1/2 teaspoon pumpkin pie spice

1 and 1/2 teaspoons baking powder

1/4 teaspoon salt

1 and 1/2 baking soda

3 and 1/2 cups all purpose flour


8 ounces softened cream cheese

12 tablespoons unsalted butter, softened

1 teaspoon vanilla extract

1/8 teaspoon cinnamon

pinch salt

5 cups Dixie Crystals Confectioners Sugar


Preheat your oven to a bit less then 400 degrees, (about 380 to 390).  I have a convection oven so I placed the dial just before the 400 mark.  Line 7 baking sheets with parchment paper or silicone liners.  If you don’t have 7 baking sheets, just rotate them.  Set aside.

In the bowl of your mixer, beat together the butter and brown sugar until combined.

Add in the eggs, one at a time.  Add the vanilla extract.

Add the pumpkin and the milk and mix well.

Combine the dry ingredients together and whisk until mixed.

Add the dry ingredients and mix until just combined.  Do not over mix.

With a small scoop, scoop 8 whoopies per pan.  They will spread somewhat.

Bake the whoopies for 5 minutes, then rotate the pan and bake for 4 to 6 more.  The cookies will spring back in the middle and be lightly browned when done.  Be careful not to over bake them.

Cool them on a wire rack and do not fill until they are completely cool. You will have 7 pans of whoopies. (About 52 total)

While the cookies are baking, make the filling.

In the bowl of your mixer, beat the butter and cream cheese.  Add the vanilla, salt and cinnamon.

Slowly add in the confectioners sugar and beat until smooth and creamy.

Use the same size scoop that you used for the cookies to fill the whoopies.

It will be a hefty amount of filling, but this is the best part in my humble opinion 🙂

Store the whoopies in an airtight container for up to 3 days.  Freeze any leftovers. They freeze very well and thaw out beautifully 🙂

Enjoy these amazing bites of heaven 🙂


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