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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16 Responses to “Homemade Milky Way Candy Bars”

  1. #
    1
    KV — October 20, 2010 at 1:28 pm

    those look good too. Are homemade butterfingers next? I have a recipe I’m going to try out soon.

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    2
    Jen — October 20, 2010 at 2:41 pm

    Butterfingers would be tasty, but I’ve got something else coming on Friday…

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    3
    amanda @ fake ginger — October 20, 2010 at 6:00 pm

    OH YUM! I really want to try these but I’m horrible at dipping things too.

  4. #
    4
    oneordinaryday — October 21, 2010 at 12:25 am

    This is exactly what my son’s been asking me to do. You’re making it hard to say no – they look perfect!

  5. #
    5
    Kimmy Bingham — October 21, 2010 at 1:03 am

    Why do you tempt me so? Milky Ways are my favorites. This is so worth trying 🙂

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    Smitten Sugar — October 21, 2010 at 2:47 pm

    Yum these look delicious! I love Milky ways

  7. #
    7
    Eliana — October 21, 2010 at 8:22 pm

    Well they look pretty perfect to me! And super delicious too.

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    8
    Kerstin — October 22, 2010 at 4:11 am

    I’m so intrigued by the cool whip/chocolate mixture for the filling! These look so yummy and addicting!

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    9
    Miss Yunks — October 22, 2010 at 4:34 pm

    These look so cute and much easier than the milky ways and snickers I made a few months ago. I made mine in muffin wrappers so I didn’t dip them, just layered the chocolate, nougat, caramel, and chocolate! They came out pretty tasty but was a lot of work!

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    10
    Rachael Pergler — October 26, 2010 at 1:31 am

    I just tried these and they didn’t come out as I’d hoped. The chocolate and whipped cream mix was too sticky and wouldn’t harden. Did I do something wrong? Also what if you can’t find kraft caramel?

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    11
    Jen — October 26, 2010 at 11:41 am

    Rachael – Sorry to hear they didn’t turn out for you. The center part was a bit sticky while dipping and wasn’t super hard… Any caramel would work for this recipe, I just use the Kraft kind that comes individually wrapped.

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    12
    K — November 2, 2013 at 7:41 pm

    I would put melted chocolate in the pan first, freeze, then the chocolate mixture, then the caramel. Then you can spoon melted chocolate on top. Would this work? (It solves the dipping problem too!)

    • beantownbaker — November 3rd, 2013 @ 12:36 pm

      That could definitely work… The caramel might ooze out when you gut them though… Let me know how it goes if you try it.

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    Rick — October 31, 2014 at 11:23 am

    I hope you are not using Cool Whip which is all trans-fat and high fructose corn syrup. I’m looking for a healthier alternative to the store bought Milky Way. Perhaps a recipe for homemade whip ?

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    Linda — December 23, 2015 at 1:42 pm

    These were a DISASTER. I wasted my morning and a lot of ingredients. The chocolate mixture was so sticky when cutting into squares. The directions did not state whether to add water to the caramels when melting so I didn’t…the caramels ended up thick and so sticky, I had trouble putting it on the chocolate layer. Dumped the whole mess out since I didn’t want to waste a bag of milk chocolate chips to coat them. I have been baking my entire life (60 +) and never had a recipe go like that.

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