Nana Bessie's Whoopie Pies

Nana Bessie's Whoopie Pies

pfogg 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!"


1 h 20 m servings 531 cals
Serving size has been adjusted!

Original recipe yields 24 servings



  • Calories:
  • 531 kcal
  • 27%
  • Fat:
  • 32.2 g
  • 49%
  • Carbs:
  • 58g
  • 19%
  • Protein:
  • 5.5 g
  • 11%
  • Cholesterol:
  • 50 mg
  • 17%
  • Sodium:
  • 215 mg
  • 9%

Based on a 2,000 calorie diet

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  • Prep

  • Cook

  • Ready In

  1. Preheat oven to 350 degrees F (175 degrees C). Line baking sheets with parchment paper.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.
  7. 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.
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  1. 12 Ratings


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.

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 ...

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.

I'd add some marshmallow fluff to the filling!

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 ...

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...

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...

They were pretty good different from what I had expected but good though in a different way! Very chocolately!

very good loved the cream inside nice soft cookie