Pumpkin Whoopie Pies with a Whipped Cinnamon Filling

I feel like I’m in a blogging funk. I hope you all aren’t catching my vibe…. are you? Fall is here and all I want to do it bake, make, and sniff the air. I have a million projects done and photographed but I’m struggling to get them posted. What’s my deal? While I figure out how to get motivated, you better figure out how to get motivated to make these. I loved them!
I cracked open my first can of pumpkin this season and I couldn’t be more pleased with the first thing I chose to make. Whoopie Pies! Just the name makes me smile. Now that I have an open can you better believe there is a whole slew of pumpkin recipes coming your way.
Pumpkin Whoopie Pies recipe
Pumpkin Whoopie Pies recipe

Pumpkin Whoopie Pies with a Whipped Cinnamon Filling

Recipe slightly adapted from Very Best Baking
Makes 2 dozen pies
For the cookies:
1/2 cup (1 stick) butter, softened
1 1/4 cups granulated sugar
2 eggs, at room temperature
1 cup pumpkin puree

1 teaspoon vanilla extract

2 cups flour
1 tsp. baking powder
1 tsp. baking soda
1 tsp. ground cinnamon
1/2 tsp. salt

For the filling:
1/2 cup (1 stick) salted butter, softened
1/3 cup whipping cream, at room temperature
1/2 tsp cinnamon
1 tsp vanilla bean extract
2 1/2 to 3 cups powdered sugar
Preheat the oven to 350 degrees. In a large bowl, or the bowl of your stand mixer with the cookie paddle attached, beat the butter and sugar on medium speed until light in color and fluffy, about 3 minutes. Add the eggs and mix to incorporate. Add the pumpkin and vanilla and mix to combine. Sprinkle the flour over the top of the butter mixture and then sprinkle the baking powder, soda, cinnamon, and salt over the flour. Mix until well incorporated, about a minute. Using a one-ounce scoop, scoop the batter onto a parchment lined baking sheet. Bake for 10-12 minutes until the cookie springs back slightly when touched.
For the filling: Use a stand mixer or electric hand mixer to beat the butter, whipping cream, cinnamon, and vanilla bean extract with the wire whisk attachment.. Beat at medium-high speed until very light and fluffy, about 5 minutes. Add the powdered sugar and beat for another 3-5 minutes. The filling will be very fluffy and a medium-thin consistency. If the icing is too thick, add a touch of cream and beat again. If it is too thin add a little more powdered sugar and beat again.

Spread a tablespoon of filling onto flat side of one cookie; top with flat side of second cookie to make a sandwich. Repeat with remaining cookies and filling. Store in covered container.

Using a scoop makes the cookies nice and round. If you don’t have a scoop just take a little time and use two spoons to transfer the dough to the baking sheet. The more uniform the scoops of dough the prettier your cookies will be.
Not sure what vanilla bean paste is? I explained it in THIS post. Vanilla extract is a great substitute.
The cookies are delicious without the filling too. My husband who is not a cinnamon fan liked the cookies plain and so did my kids. That being said, the filling is phenomenal (to a cinnamon lover like myself). I am trying to think of more ways to use it! Any thoughts?
Pumpkin Whoopie Pie recipe
Pumpkin Whoopie Pie recipe


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38 Recipes for Busy Moms
17 Responses
  1. solarpoweredyogi.com

    Gurrrrrrrrl, I am feeling you with the blogging funk. I have literally thousands of photos to sort and process and a million things to write about, but I’m just like, no, it’s baking and reading in pajamas time.

  2. Jess from Coxs Corner

    Oh man, these look amazing! I love whoopie pies! I’m sorry you’re in a funk…I never got that vibe off of you, so that’s good!

  3. Mishi

    Made these for my grandfather’s birthday. The cookie parts are soooo perfect. <3 I love the consistency, and now the house smells like pumpkin... mmm... <3

  4. BeccaMarie

    How could I have not seen this post? I’ve never made whoopie pies, pumpkin would be a great place to start. Especially since we just pulled out nine pumpkins from our garden. Or maybe I’ll just used canned pumpkin. I don’t know. Can I make pumpkin puree out of a pumpkin? uuuuh, I don’t feel very smart right now…

  5. Jonie Marie

    Be still my heart. These look delicious! I think if I made them that I would eat the whole batch.

    Thanks for linking up to Point of View!

  6. bumblebee-bakes

    Made these tonight! The one change I made was that I doubled the amount of cinnamon in the filling because I’m a cinnamon lover. What a great recipe, thank you so much for sharing! This is the first time I’ve ever made whoopie pies (or had one!) and my family loved them.

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Bless This Mess - About Me

I’m Melissa, and I want to help you feed your family wholesome food.

As a hobby farmer and mom of five, I’m all about keeping it simple in the kitchen. I want healthy meals that feed my family well, and then I want to get back to my (messy) life. Let’s work together to find something yummy for your dinner table.

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