Two-Way Chocolate Whoopie Pies

Posted by Anna on 02 Aug 2007 at 08:27 pm | Tagged as: Sandwich Cookies

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”. When I looked at the recipe, I could tell the cookies were really just gussied up 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.

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.

Whoopie Pies Cut.jpg

Two-Way Chocolate Whoopie Pies

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 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

Preheat oven to 350 degrees F. Line two cookie sheets with parchment or non-stick foil.

Stir together the flour, baking powder, baking soda, salt and cocoa powder. Set aside.

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.

Drop the cookies by quarter cupfuls onto the cookie sheets - 7 or 8 cookies per sheet.
If you plan on using the mascarpone filling, I recommend making the smaller size (8 cookies per sheet) cookies.

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.

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.

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.

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.

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.
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.

15 Responses to “Two-Way Chocolate Whoopie Pies”

  1. on 03 Aug 2007 at 6:13 am 1.Gigi said …

    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. on 03 Aug 2007 at 8:48 am 2.ThereseB said …

    Too funny Anna!

    I played Bunco last night. It was a Wine/Cheese Bunco. Today I have a headache from all that red wine!
    I LOVE WHOOPIE PIES…I have an Amish recipe that I use too. Your’s looks JUST like that recipe!!!
    WHOOPIE PIES ARE SIMPLY AMAZING!!!!! I will have to compare our recipes. Your filling is very different though. I will have to check it out.
    How are you all feeling????
    Take care!

  3. on 03 Aug 2007 at 11:32 am 3.amela said …

    I made a whoopie pie recipe a few years ago that I got from Food & Wine. I had never heard of them before, and honestly only made them because I liked saying “whoopie!” My filling wasn’t as fluffy looking as yours; it was creamier than oreo filling, but definitely not hostess cupcake like, which is what your’s looks like to me. That recipe is sitting next to my computer for some reason and I keep saying I’ll make them again. That peanut butter filling idea sounds good!

    Amy

  4. on 03 Aug 2007 at 11:40 am 4.Candace B said …

    I just bought these cute ice cream sandwich makers at the Williams-Sonoma Outlet - http://www.williams-sonoma.com/products/sku7999436/index.cfm?bnrid=3100117&cm_ven=WS&cm_cat=General&cm_pla=SiteMap&cm_ite=Products&CM_REF=http%3A%2F%2Fwww.google.com%2Fsearch%3Fhl%3Den%26q%3Dwilliams-sonoma%2Bice%2Bcream%2Bsandwich%26btnG%3DGoogle%2BSearch&flash=on
    (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?

  5. on 03 Aug 2007 at 1:59 pm 5.Anna said …

    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.

    http://www.williams-sonoma.com/recipe/recipedetail.cfm?objectid=6B38C795%2D9957%2D419C%2D83B98DAFCAC64786

  6. on 03 Aug 2007 at 2:02 pm 6.Anna said …

    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.

  7. on 03 Aug 2007 at 7:04 pm 7.Squishy said …

    These look so great. Awesome, I will definatley give these a go.

  8. on 05 Aug 2007 at 11:29 am 8.Amy said …

    Anna,
    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.

  9. on 08 Aug 2007 at 2:34 pm 9.Jennifer Palmer said …

    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

  10. on 08 Aug 2007 at 2:45 pm 10.Anna said …

    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).

  11. on 13 Sep 2007 at 10:54 am 11.Jen said …

    Too Funny! I just saw Whoopie Pies on Martha Stewart today! A Maine company, Cranberry Island Kitchen was featured. They looked soo good!

  12. on 14 Sep 2007 at 1:55 pm 12.Jennifer said …

    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!

  13. on 14 Sep 2007 at 2:10 pm 13.Anna said …

    Hi Jennifer,

    I sent you a suggestion via email.

  14. on 17 Jun 2008 at 4:11 pm 14.Joanna said …

    If you wanna try some of the best whoopie pies, http://www.wickedwhoopies.com 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.

  15. on 19 Jun 2008 at 8:42 am 15.Esther said …

    Can the whoopie pies be frozen for later use?

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