Rating: 3.91 stars
22 Ratings
  • 5 star values: 7
  • 4 star values: 8
  • 3 star values: 6
  • 2 star values: 0
  • 1 star values: 1

I've never been able to find whoopie pies this good! My grandmother always made them -- the secret is in the filling. I give them out at Christmas time, everyone looks forward to them. The recipe makes extra filling -- doubles as a great cake frosting!

Recipe Summary test

prep:
30 mins
cook:
20 mins
additional:
30 mins
total:
80 mins
Servings:
24
Yield:
24 whoopie pies
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Ingredients

24
Original recipe yields 24 servings
The ingredient list now reflects the servings specified
Ingredient Checklist

Directions

Instructions Checklist
  • Preheat oven to 350 degrees F (175 degrees C). Line baking sheets with parchment paper.

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  • To make cookies, beat 2/3 cup of vegetable shortening with 2 cups of sugar in a large mixing bowl with an electric mixer until the mixture is creamy. Beat in eggs and 2 teaspoons of vanilla extract until thoroughly combined. Whisk together 4 cups of flour, the cocoa powder, and baking soda until thoroughly mixed, then beat the flour mixture into the vegetable shortening mixture in several additions, alternating with the milk. Beat dough just until smooth.

  • Drop dough by tablespoon onto the prepared baking sheets, about 2 inches apart, making the cookies as round as possible. Recipe should yield about 48 cookies.

  • Bake in the preheated oven until the cookies are set in the middle, 15 to 20 minutes. Watch carefully to avoid burning the cookies. Allow cookies to cool for several minutes on baking sheets before removing to finish cooling on racks.

  • To make the filling, pour 3 cups of milk into a large saucepan over low heat, and whisk in 9 tablespoons of flour until smooth. Allow the mixture to come to a simmer, whisking constantly, until as thick and smooth as pudding, about 3 minutes. Place the thickened mixture into the refrigerator to cool, about 30 minutes.

  • In a large mixing bowl, beat 1 1/2 cup of vegetable shortening with the butter until thoroughly combined, then beat in 2 1/4 cup of sugar and 1 tablespoon vanilla extract until the mixture is thoroughly combined. Beat the cooled milk mixture into the butter mixture until smooth and fluffy, 1 to 2 minutes.

  • Choose 2 cookies of the same size, and spread a thick layer of filling on the flat side of a cookie; top with remaining cookie. Repeat with remaining cookies and frosting.

Nutrition Facts

531 calories; protein 5.5g; carbohydrates 58g; fat 32.2g; cholesterol 50.1mg; sodium 214.6mg. Full Nutrition
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Reviews (23)

Most helpful positive review

Rating: 5 stars
12/03/2011
I had a similar recipe years ago that i got from an old Pennsylvania Dutch cookbook but had lost it much to my disappointment. I never liked the whoopie pies with the marshmallow cream filling because it was always way too sweet so i'm really happy to find this recipe. Thanks! Read More
(25)

Most helpful critical review

Rating: 3 stars
11/28/2011
The cakes came out great but no one really liked the filling. The texture was perfect but it was missing flavor. Followed recipe exactly. Might try this but with different filling recipe. Read More
(39)
22 Ratings
  • 5 star values: 7
  • 4 star values: 8
  • 3 star values: 6
  • 2 star values: 0
  • 1 star values: 1
Rating: 3 stars
11/27/2011
The cakes came out great but no one really liked the filling. The texture was perfect but it was missing flavor. Followed recipe exactly. Might try this but with different filling recipe. Read More
(39)
Rating: 5 stars
12/03/2011
I had a similar recipe years ago that i got from an old Pennsylvania Dutch cookbook but had lost it much to my disappointment. I never liked the whoopie pies with the marshmallow cream filling because it was always way too sweet so i'm really happy to find this recipe. Thanks! Read More
(25)
Rating: 3 stars
07/31/2012
Cakes were great!! Didn't care for the filling much. If you do decide to make this filling, I would suggest dividing it in half. Makes way too much, even with being generous. Read More
(7)
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Rating: 5 stars
08/22/2012
I'd add some marshmallow fluff to the filling! Read More
(4)
Rating: 3 stars
03/06/2013
The cakes were good but the icing recipe was off. I agree with other reviewers that there was an excess of bland flavored icing. I tweaked it and the result was delicious...essentially I would follow the recipe but change the icing proportions as follows: 1 cup milk 3 tablespoons of all-purpose flour 3/4 cups vegetable shortening 3/4 cups butter 2 cups white sugar 1 Tablespoon of vanilla (or almond) extract Read More
(4)
Rating: 4 stars
08/05/2012
These are delicious the only drawback for me was the richness of the filling. I really piled it on the cakes and it was just too much. I will definately put less filling next time. I also used a tip from another whoopie recipe and wrapped each one in plastic wrap then refrigerated them. They are good straight from the fridge. Read More
(3)
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Rating: 4 stars
09/20/2012
They were pretty good different from what I had expected but good though in a different way! Very chocolately! Read More
(1)
Rating: 3 stars
09/25/2012
Filling was a total flop but the cakes were really good. The filling was one of the most disappointing (and time consuming) of my baking endeavors. Will use my grandmothers recipe next time for the filling but might stick with this recipe for the cakes. I definitely learned from this recipe though! Read More
(1)
Rating: 3 stars
05/17/2016
Thought the cake was ok not the best I had trouble with the frosting and didn't end up making it instead I put vanilla Icecream in the center I would recommend you to add melted chocolate o top if u are using Icecream as the chocolate whoppie pie tastes a little bland with out it Also if it is hard to make perfect cirles for the pies so I just spread it out in an even layer on a greased cookie sheet and then cut squares ( could also cut into circles) Read More