Mini Pumpkin Whoopie Pies (October Cookie Carnival)

This month’s Cookie Carnival recipe is for pumpkin whoopie pies. When I saw the email, I thought they’d be Pumpkin with a cream cheese filling. I’ve seen quite a few recipes floating around for those. But these are chocolate cookies with pumpkin filling. That way they’re black and orange for Halloween 🙂 The recipe is from Martha and you can even watch her make them with Cookie Monster here.

I’ve never made whoopie pies before so this was fun for me. The chocolate cookie batter is very chocolatey and delicious 🙂 The filling is also great. It only uses 1/4 cup of pumpkin, so it looks like I’m going to be making something else pumpkin-ey soon. I’m looking forward to that! Next time I’ll definitely make a double batch of the filling. I thought the cookie somewhat overwhelmed the pumpkin filling. But overall, these were great and I’ll definitely be making these again. Probably very soon.

Mini Pumpkin Whoopie pies – from Martha Stewart – makes ~20
For the Cookies1 3/4 cups all-purpose flour
3/4 cup unsweetened cocoa powder (not Dutch-process)
1 1/2 teaspoons baking soda
1/2 teaspoon coarse salt
1 tablespoon unsalted butter, softened
1/4 cup vegetable shortening
1/2 cup granulated sugar
1/2 cup packed dark-brown sugar
1 large egg
1 cup whole milk – I used soymilk
1 teaspoon pure vanilla extract

For the Filling4 ounces cream cheese, at room temperature
1/2 cup (1 stick) unsalted butter, at room temperature
1/2 cup confectioners’ sugar
1/4 cup canned solid pack pumpkin
Pinch of cinnamon
Pinch of nutmeg

Prepare cookies: Preheat oven to 375 degrees. Sift together flour, cocoa powder, baking soda, and salt into a medium bowl; set aside.

Place butter, shortening, and sugars into the bowl of an electric mixer fitted with the paddle attachment. Mix on high speed until smooth, about 3 minutes. Add egg; mix until pale and fluffy, about 2 minutes. Mix in half the flour mixture, then the milk and vanilla. Mix in remaining flour mixture.

Drop about 2 teaspoons dough onto baking sheets lined with parchment paper, spacing 2 inches apart. Bake until cookies spring back when lightly touched, 12 to 14 minutes. Transfer baking sheets to wire racks and let cool 10 minutes. Remove cookies from baking sheets and transfer to wire racks using a spatula; let cool completely.

Prepare filling: In the bowl of a mixer fitted with the paddle attachment, whip together cream cheese, butter and confectioners’ sugar on medium speed until smooth, about 3 minutes. Add pumpkin, cinnamon, and nutmeg; whip until smooth, scraping down the bowl as necessary.

Pipe or spoon about 2 teaspoons filling on the flat sides of half the cookies. Sandwich with remaining cookies, keeping the flat sides down.

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15 Responses to “It’s a boy! Dipped Oreo Pops”

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    Cupcake Activist — May 13, 2010 at 6:08 pm

    Cute idea and they look so easy to make. Must try.

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    Cupcake Activist — May 13, 2010 at 6:08 pm

    And the stick makes them perfect for milk dipping.

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    jess @ pen n' paperflowers — May 13, 2010 at 6:48 pm

    oh my…i’ve tried my hand at these and just about every oreo ended up cracking when i tried to insert the stick. *frowny face* not even dipping the sticks first seemed to help? do you have any suggestions on how to slide them in without any hiccups. *wink*
    thank you SO much for your help…yours came out adorable!

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    We Are Not Martha — May 13, 2010 at 7:30 pm

    Wow, these are such a great favor idea! They look easy, but impressive (and delicious)!

    Sues

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    Sarah — May 13, 2010 at 8:19 pm

    I am loving all of these new parents/new baby posts, because friends of ours just had a baby boy last week and I can just do everything you’re doing! 🙂

    Jess@pen – are you using Double Stuffed Oreos? If you’re using regular Oreos, maybe the center isn’t thick enough to support the lollipop stick between the cookie ends. Or maybe the lollipop stick isn’t thin enough (do they even make different sizes?). Just thinking out loud. Good luck. 🙂

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    Jen — May 13, 2010 at 9:11 pm

    jen@pen – I agree with Sarah, be sure to use double stuff Oreos and thin sticks. You’ll notice that the craft store has at least two thicknesses of sticks. You want the thinnest ones. I did slide the sticks in slowly but didn’t have any issues with breaking cookies.

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    Kara — May 13, 2010 at 10:26 pm

    Why must this kind of thing be posted when I’m trying to lose weight? 😉

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    Kim @ Frost Me! — June 8, 2010 at 10:37 pm

    YUM! I love the idea of doing the initial on them!

    Kim @ http://frostmeblog.blogspot.com
    party inspiration

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    Shawnda — February 22, 2013 at 2:05 am

    Just choose to tell you a piece of writing is really as awesome. All of the picture quality in your own place is definitely fascinating and are able to feel you’re an experienced for this idea. Fantastic along with your agreement i can to seize ones give food to to continue modified together with upcoming publish. Thx one million and you need to maintain this worthwhile succeed.

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    facebook.com — August 8, 2013 at 12:54 pm

    Awesome post.

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    Pam — February 23, 2014 at 5:19 pm

    How far ahead can you make these and will the Oreo get soggy ?

    • beantownbaker — February 23rd, 2014 @ 8:45 pm

      We made them a week in advance and the Oreos did not get soggy.

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    Christina — March 23, 2014 at 8:58 pm

    I can totally see the hiccups @jess, the Double Stuf Oreos have a far more thin and brittle cookie than the original Oreos. They crumble, split and crack very easily, I would imagine irregardless of stuffing volume, the structural integrity of the original Oreo cookie would hold up better for this project.

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    Lana — January 29, 2016 at 3:40 am

    Can u freeze them?

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    Leah — October 11, 2022 at 7:26 pm

    Hi just wanted to say I have made these every year since 2009 when you posted them, still love them just as much!

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