Chocolate Whoopie Pies with Pumpkin Custard Filling

happy halloween

So…I guess there was a storm this week? It was crazy, you guys! Thankfully my block was completely fine. We lost our Internet on Monday night and into Tuesday afternoon, but other than that, we were pretty alright. We watched the wind whipping everything around outside, ate lots of good food, had a few drinks, and watched some movies. The bodega down the street from us was open during the entire thing, supplying the entire neighborhood with plenty of chips, soda, cookies, and beer to make it through. I know that I am extremely lucky and so much of New York City, hell, the entire East coast and especially so much of the Caribbean have been completely destroyed by this massive storm. I am extremely thankful that we were able to ride it out without having to worry about our own personal safety, but my thoughts are with all of those that are still without power, phone service, or even without food and running water, and I hope that all of the disaster relief efforts get all of the support that they need during the next few weeks, and possibly even the next few months. If you are able, please donate a few dollars to the Red Cross (or contact local resources in your area – everyone needs donations not only in monetary form, but in the form of time and effort from volunteers in the community) in order to help speed up these disaster recovery efforts, and let me know how the rest of you are doing! I know that a good percentage of you guys are on the East coast – I’ve been following Twitter and Instagram all week to see how everyone’s doing, but let me know what’s going on in your neck of the woods!

Chocolate Whoopie Pies with Pumpkin Custard FillingThe view from my balcony the morning before the storm hit.

Currently, I’m sitting at home, trying to find a car service to take me into Manhattan. It’s incredibly frustrating! In the meantime, why don’t I share these whoopie pies that I made for my friend Val and Tom’s Halloween party that I posted about on Monday? I really liked them, especially the custard filling. They were just a bit different – I think that the custard was a welcome change from the usual buttercream, plus you don’t even need to use any food coloring to get that fun black and orange coloring for your holiday festivities. The custard has many other uses, too – put it in yogurt, eat it with some ice cream, or even with some homemade granola. ‘Tis the season for pumpkin everything, and even if you are one of those people, like me, I’ll admit, who doesn’t necessarily jump at the first sight of pumpkin, these are subtle enough for everyone to enjoy.

Chocolate Whoopie Pies with Pumpkin Custard Filling
The beer braised ribs that we made on Monday night (recipe to come, of course).

Chocolate Whoopie Pies with Pumpkin Custard Filling
Enjoyed some cocktails while watching the trees whip against our windows.

Chocolate Whoopie Pies with Pumpkin Custard Filling
And, of course, I couldn’t stop cooking and made pumpkin cinnamon rolls (again, recipe to come) during the storm.

Chocolate Whoopie Pies with Pumpkin Custard Filling
Bring your custard ingredients to a simmer, and cook until thickened, about 10 minutes over medium-low heat, stirring frequently. Strain through a mesh sieve, then refrigerate until cooled overnight. The next day, combine your whoopie pie ingredients and make your dough.

Chocolate Whoopie Pies with Pumpkin Custard Filling
Place scoops of your dough onto your baking sheets and bake at 350 degrees F for 10-12 minutes, until set. Allow to cool completely before sandwiching with the chilled custard.

Chocolate Whoopie Pies with Pumpkin Custard Filling
Place in the fridge until ready to use, then serve and enjoy Halloween!


Chocolate Whoopie Pies with Pumpkin Custard Filling
Prep time: 
Cook time: 
Total time: 
Serves: 30 small whoopie pies
Soft chocolate cookies with a rich pumpkin custard in between.
For the Pumpkin Custard:
  • 2 eggs, room temperature
  • 4 egg yolks, room temperature
  • 1 cup firmly packed dark brown sugar
  • 1½ cups pure pumpkin puree
  • 1 cup half and half, room temperature
  • 1 tablespoon vanilla extract
  • ½ teaspoon kosher salt
  • ½ teaspoon ground cinnamon
  • ¼ teaspoon freshly grated nutmeg
  • ¼ teaspoon ground cayenne pepper
  • 5 tablespoons unsalted butter, cubed
For the Whoopie Pies:
  • 2 cups all-purpose flour
  • ½ cup cocoa powder
  • 1¼ teaspoon baking soda
  • 1 teaspoon kosher salt
  • ½ cup unsalted butter, cubed
  • 1 cup granulated sugar
  • 1 egg, room temperature
  • 1½ teaspoons vanilla extract
  • 1 cup whole milk
  1. In a non-stick pot, whisk together your eggs, egg yolks, and brown sugar until combined. Heat over medium and continue to whisk until the sugar has dissolved, then add in the pumpkin, half and half, vanilla, and spices. Whisk to combine, then bring to a simmer. Whisk continuously for the next 8 minutes or so, until quite thickened, then remove from the heat and add in your butter, one cube at at time, until fully combined. Press the custard through a mesh sieve, place in a bowl, and cover with plastic wrap, being sure to press the plastic to the custard so that it does not form a skin. Refrigerate for a minimum of 6 hours, but preferably, overnight.
  2. Preheat your oven to 350 degrees F. Whisk together the flour, cocoa powder, baking soda, and salt in a small bowl and set aside. In the bowl of your mixer, beat together the butter and sugar until light and fluffy, about 3 minutes, then add in the egg, beat until combined, followed by the vanilla.
  3. Add in the flour and milk in alternating intervals, starting and ending with the flour. Beat until just moistened and scrape down the sides of the bowl as necessary. Line your baking sheets with parchment and scoop out 2 to 3 teaspoon sized balls of dough and place on the sheets. Leave about 2 inches of space between each one, as it will spread out just a bit. Bake for 12 minutes or so, until set. Allow to cool completely before sandwiching with the custard. The finished whoopie pies may be stored in an airtight container in the refrigerator for up to 2 days.


14 Responses

  1. JulieD says:

    These whoopie pies are gorgeous!! Glad you are safe!!

  2. Heathre says:

    Not only do those look good, but all the ingredients are real!

  3. I want those cinn rolls!!I have been getting really into yeast bread making lately and I am in search of ‘the perfect’ cinn roll recipe. And those look like they’d work quite perfectly :)

    The cookies – I made pumpkin whoopie pies a few weeks back and need to try chocolate. They look crazy good!

    Glad you are SAFE!

  4. These look incredible! And thankfully, here in Somerville, Mass. we didn’t get too much damage from the hurricane. Glad you’re OK and have power!

  5. Skye says:

    These look incredible! I might make them sometime for my best friend, who isn’t a big fan of pumpkin pie but hasn’t tried much else in the way of pumpkin, and I’m trying to convert her into a pumpkin lover. :) I’m making pumpkin pasta tonight for our pumpkin carving get-together, and I made pumpkin mousse for dessert, but I’m worried it’s too similar to pumpkin pie filling for her taste. :-/

    I’m in Northern VA and thankfully I didn’t suffer any flooding or power loss. I’m so glad you guys are safe, too.

  6. Deb says:

    Glad to hear your storm experience was uneventful! I is quite nerve wracking to watch the storm and aftermath from 3000 miles away.

    I am thinking these tasty Chocolate Pumpkin Whoopie Pies would be perfect for a party I’m attending later this month. It is an enchanting autumn dessert both adults and kids will enjoy!

  7. Glad you made it through the storm all right! Also, could you please send me those pumpkin cinnamon rolls? :) At the very least, I’m looking forward to the recipe!

  8. Glad to hear the storm wasn’t bad for you. Can’t wait to see the pumpkin rolls- they look yummy. I am for sure going to have to try that custard. It sounds wonderful and unique.

  9. Elizabeth says:

    Chocolate and pumpkin sound amazing together! These look great!

  10. Halloween is over but I’d still make these every single day! And I totally need a bite of those pumpkin cinnamon rolls!

  11. rhoda herzog says:

    Sydney, I just have to tell you that I baked (again) your delicious chocolate crinkle cookies, to serve at a reception after one of the movie we plan to show at the 12th annual Jewish Film Festival here in Mobile.
    The cookies are so pretty – chocolate with streaks of white and cake-like. They look lovely on a platter. Do you have any other easy and beautiful cookies to recommend?
    Glad you are surviving Sandy , you are indeed lucky. Here in Alabama we are used to those bad hurricanes…

  12. Lynna says:

    YUM. The custard is tempting me. I can`t wait for the rib and cinnamon roll recipes!

  13. […] Chocolate whoopie pies with pumpkin custard filling. (via The Kitchn) […]

  14. […] As a pregnant lady, I think I now have every right and freedom to indulge in every food craving I have  So today, I bring you a recipe for Chocolate Whoopie Pies courtesy of Crepes of Wrath. […]

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