Two Way Chocolate Whoopie Pies

A few years ago, I took a food and wine pairing class with Andrea Immer. One of the recipes she gave the class was “Soft Chocolate Sandwich Cookies with Cherries and Mascarpone”. In other words, a fancy version of Chocolate Whoopie Pies — big, soft, fat, Amish chocolate cookies filled with mascarpone and dried fruit instead of the usual shortening based cream filling. Filling Whoopie Pies with mascarpone seemed brilliant, but I never thought about the cookies again until today, when I found the handout with the recipe. I decided to make the cookies for Todd.

Two Way Whoopie Pies

Somewhere along the way, I mentally tallied up the price of filling ingredients — mascarpone, dried cherries, whipping cream…. and decided that rather than go Italian, I’d go Amish. I ended up making basic Chocolate Whoopie Pies, courtesy of the King Arthur Cookie Book. Below is what they looked like. Perhaps they dream of a better lifestyle? If you’d like to give them that, I’ve included the mascarpone-dried cherry filling as well. If you use that one, make the cookies smaller and follow the directions below for serving.

Two-Way Chocolate Whoopie Pies
Prep time
Cook time
Total time
Two Way Chocolate Whoopie Pies -- You can make them with traditional filling or make them with a mascarpone based filling.
Recipe type: Dessert
Cuisine: American
Serves: 10
  • 2 cups all purpose flour
  • 1 teaspoon baking powder
  • 1 teaspoon baking soda
  • 1 teaspoon salt
  • 6 tablespoons Dutch process cocoa
  • 1/2 cup shortening
  • 1 cup brown sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 1 cup milk
Amish Filling:
  • 1 cup shortening
  • 1 cup powdered sugar
  • 4 ounces (1 1/3 cups) Marshmallow Fluff or Crème
  • 1/4 teaspoon salt dissolved in 1 tablespoon water
  • 1 1/2 teaspoons vanilla
Fancy Italian Mascarpone Filling:
  • 1 cup dried cherries
  • 1/2 cup plus 2 tablespoons granulated sugar (divided use)
  • 1 cup chilled heavy whipping cream
  • 8 ounces of mascarpone cheese
  1. Preheat oven to 350 degrees F. Line two cookie sheets with parchment or non-stick foil.
  2. Stir together the flour, baking powder, baking soda, salt and cocoa powder. Set aside.
  3. In a mixing bowl, beat the shortening and brown sugar until fluffy. Beat in the egg and continue beating until very creamy and light. Beat in the vanilla. Starting with the flour mixture, add the flour mixture and milk to the butter mixture alternately, beginning and ending with flour.
  4. Drop the cookies by quarter cupfuls onto the cookie sheets - 7 or 8 cookies per sheet.
  5. If you plan on using the mascarpone filling, I recommend making the smaller size (8 cookies per sheet) cookies.
  6. Bake the cookies, one sheet at a time, for 12-15 minutes or until they appear set but still moist. Scoop them up onto a cooling rack and allow them to cool completely.
  7. Now make whichever filling you've chosen. For the Amish filling, beat together the shortening, powdered sugar, marshmallow stuff, dissolved salt and vanilla. Stuff the cookies as you would if you were Amish. Serve however you want.
  8. If you've chosen the expensive, fancy filling, do this. Measure out 2 tablespoons of the dried cherries and set them aside. Roughly chop the rest.
  9. Place 2 tablespoons of the sugar in a bowl and add the un-chopped cherries to the bowl. Shake the bowl gently to coat the cherries with sugar, then set them aside. Add the chopped cherries to the bowl and shake them so that they are coated with whatever sugar remains. Set them aside as well.
  10. In a separate bowl, beat the whipping cream and sugar until peaks form. In yet another bowl, fold 1/3 cup of the whipped cream mixture into the mascarpone cheese to lighten it, then fold this mixture into the remaining whipped cream. Spread a 1/4 thick inch layer of filling onto the bottom side of a cookie. Sprinkle on about 3/4 teaspoon of the chopped dried cherries and top with another cookie, pressing lightly to make a sandwich. Do this until you have 8 sandwich cookies. To serve, heap the cookies on a platter and serve them with the extra whipped cream and the sugared cherries which you did not chop up.
I can't remember the exact yield of this recipe but I think it made about 10 large sandwiches.

Serve the heaping tray of mascarpone stuffed Whoopie Pies with a sweet, effervescent wine such as Brachetto d'Acqui Coppo, which is what Andrea recommended. Also, don't call them Whoopie Pies.


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  1. Gigi says

    Growing up in a small town in central PA, you become accustomed to things like whoopie pies, apple butter, homemade jam and mountain pies. Now, it’s practically impossible to find stuff like that outside of a fancy schmancy gourmet market or one of the local pseudo-farmers market. Ah youth…

    Anyway, my mom used to make all kinds of whoopie pie/filling combinations (my personal favorite is chocolate with peanut butter filling). Anytime there was a bake sale or something that required a sweet treat, that was her go-to product. I have never been able to recreate the perfect dome she could get on the cookie-cake part. Maybe I’ll give them another try.

    By the way, I’m making a “24 karat gold cake” today – 12 egg yolks and no egg whites. Any experience with that type of recipe? I’m trying to recreate an amazing piece of cake I had at the shore last weekend. Really yellow and really moist with huge melt-in-your-mouth crumbs.

  2. Candace B says

    I just bought these cute ice cream sandwich makers at the Williams-Sonoma Outlet –
    (only $5 there!) and I’m thinking the cookie part of the whoopie pie would be perfect for those. Do you think it would work if I made them as a bar cookie?

  3. says

    Candace, I took a look at those ice cream sandwich cutters. They are adorable, but I am not so sure the Whoopie Pie batter would work with them because it produces a soft, puffy, cakey cookie. I could be wrong, but from the pictures, I gather you’d need a firm yet soft dough like a brownie or soft, dense flat oatmeal cookie. You may have seen this already but, WS has some recipes on their site. This one is designed for the ice cream sandwiches.

  4. says

    Therese, I hope you are recovering well today. Sounds like a wild Thursday night.

    Amy, the filling reminded me of the kind in Suzy Q’s…remember those? It was low rent, for sure. However, it worked perfectly and had just the right texture.

  5. Amy says

    I saw an ad for the new Oreo Cakesters. Have you seen them? They look (from the ad anyway) like small whoopie pies. I don’t know if they are in stores yet, but I will have to try them.
    Your whoopie pies look great. I used to love Suzy Q’s and had forgotten about them til you mentioned them.

    Amy D.

  6. Jennifer Palmer says

    Amy D.,
    Don’t bother with the Oreo Cakesters, they were a disappointment. I always prefer homemade treats, but on the other hand, I would never turn up my nose at ding dongs, or ho o’s, so when I say the oreo cakesters were bad….believe me. Jen

  7. says

    I love Oreos! They are a staple at my house. However, I did not feel compelled to buy the cakesters even though I’ve walked by them several times (they’re on the end cap at our H.E.B.). Jen, I’ll take your word on this — especially since you are open minded when it comes to snack cakes. Then again, maybe you got an older batch of Cakesters? Maybe the cakesters just taste best fresh off the line? Then again, they’re a new product so how could the box be old? I probably will stick with regular Oreos for now (and Fudge Oreos and Peanut Butter Oreos).

  8. Jennifer says

    I had these marvelous cookie sandwiches at Diseny MGM Studies, they were like whoopie pies only made with a carrot cake batter for the sandwich part and butter cream for the filling. I am dying to try to recreate them, but am unsure how to make the batter thick enough like a whoopie pie so that when I spoon it out on the sheet it does not go everywhere. What if I use a boxed mix what can I add to it baking soda or powder? Any suggestions? Thanks!

  9. Joanna says

    If you wanna try some of the best whoopie pies, mails them to your house. I have been obsessed with whoopie pies ever since I watched an episode of “Road Tasted.” The maple whoopie, chocolate chip whoopie, and raspberries and cream are my favorites. Actually, I can’t leave out the chocolate peanut butter one either. Whatever you get, you won’t be disappointed.

  10. says

    Your whoopie pie’s look excellent.
    I don’t know what I did wrong with the two way Chocolate whoopie pies but mine came out flat and they were not cooked in the 12-15 minutes that the recipe said. I didn’t use dutch chocolate – I used Hersey’s baking chocolate. What is Dutch Chocolate? I guess this recipe isn’t for me. Someone else will probably have better lucky with it.

    Instead of throwing out the batch I made – I added more Hersey’s chocolate and added some walnuts and Chocolate chips and cooked them for 20 minutes and they came out good.

  11. says

    Hi Peggy,

    I’m sorry you didn’t have any luck with this recipe. Believe it or not, the cocoa might have been the culprit. In some recipes, swapping out Dutch for Natural (the kind you used) or vice versa affects the leavening. Dutch cocoa has less acid than natural, so maybe the natural cocoa you used (which has more acid) made the batter too acidic and the cookies rose too fast and fell? Not sure. But this recipe is based on one from King Arthur so it should have worked. I will re-test it myself.

    But it’s true that swapping natural and Dutch cocoa makes a difference. For instance, I have a recipe for Tex Mex Chocolate Cookies. If I make them with Dutch cocoa, they come out flat, but if I make them with natural, the come out nice and thick. It’s actually the opposite of the situation you encountered and the recipes are both different, but the point is it makes a difference.

    When a recipe calls for Dutch chocolate cocoa, I usually use Hershey’s Dark which is pretty easy to find.

  12. says

    Thank You for your help. I will have to get some Hersey’s Dark Chocolate and try it again. It maybe a few days but I will let you know how they come out.
    Thank You again

  13. YanYanKong says

    Do you have a recipe for whoopie pies that does not require shortening or can I replace the shortening in this recipe for butter?

    And is powdered sugar same as icing sugar? Do I have to use powdered sugar or does normal white sugar work?

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